1-chloro-2,2-dimethylpropane

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of p,p'-di-t-butyl biphenyl (5.559 g, 0.021 mol) and THF (100 mL) was stirred at 0° C. under an atmosphere of argon. Lithium wire (0.021 mol, 0.15 g) was added in small pieces and the mixture was allowed to stir at 0° C. for 24 h. The mixture was cooled to -78° C. and neopentyl chloride (2.0 g, 0.01875 mol) was added dropwise. The mixture was stirred at -78° C. for 1 h, and the compound of Example g (3.17 g, 0.015 mol) was added all at once. The mixture was continuously stirred or 4 h and 50 mL sat aq NaHCO3 was added. This mixture as extracted with three 50 mL portions of ethyl acetate. The combined extracts were washed twice with water, dried (MgSO4), and concentrated. The crude concentrate was purified by HPLC eluting with 1:4 ethyl acetate/hexanes. The oxazoline was as a clear oil in 27% yield. The mixture was cooled to -78° C. The mixture was stirred at -78° C. for 1 h The mixture was continuously stirred or 4 h was added This mixture as extracted with three 50 mL portions of ethyl acetate The combined extracts were washed twice with water dried (MgSO4) concentrated The crude concentrate was purified by HPLC eluting with 1:4 ethyl acetate/hexanes

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of p,p'-di-t-butyl biphenyl (5.559 g, 0.021 mol) and THF (100 mL) was stirred at 0° C. under an atmosphere of argon. Lithium wire (0.021 mol, 0.15 g) was added in small pieces and the mixture was allowed to stir at 0° C. for 24 h. The mixture was cooled to -78° C. and neopentyl chloride (2.0 g, 0.01875 mol) was added dropwise. The mixture was stirred at -78° C. for 1 h, and the compound of Example g (3.17 g, 0.015 mol) was added all at once. The mixture was continuously stirred for 4 h and 50 mL sat aq NaHCO3 was added. This mixture was extracted with three 50 mL portions of ethyl acetate. The combined extracts were washed twice with water, dried (MgSO4), and concentrated. The crude concentrate was purified by HPLC eluting with 1:4 ethyl acetate/hexanes. The oxazoline was as a clear oil in 27% yield. The mixture was cooled to -78° C. The mixture was stirred at -78° C. for 1 h The mixture was continuously stirred for 4 h was added This mixture was extracted with three 50 mL portions of ethyl acetate The combined extracts were washed twice with water dried (MgSO4) concentrated The crude concentrate was purified by HPLC eluting with 1:4 ethyl acetate/hexanes

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: CrCl3(THF)3 (a product of Aldrich Co.) and 2,2-dimethylpropyl magnesium chloride (synthesized from 1-chloro-2,2-dimethylpropane, a product of Aldrich Co. and magnesium, a product of Wako Pure Chemicals Co.) were reacted according to a method described in J. Chem. Soc., Dalton Trans., 770 (1973) to prepare tetrakis(2,2-dimethylpropyl)chromium(III). This compound was dissolved in distillation-purified hexane to obtain a solution of 0.10 mol/liter, 5.20 g/liter. ) were reacted to obtain a solution of 0.10 mol/liter, 5.20 g/liter

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: CrCl3(THF)3 (a product of Aldrich Co.) and 2,2-dimethylpropyl magnesium chloride (synthesized from 1-chloro-2,2-dimethylpropane, a product of Aldrich Co. and magnesium, a product of Wako Pure Chemicals Co.) were reacted according to a method described in J. Chem. Soc., Dalton Trans., 770 (1973) to prepare tetrakis(2,2-dimethylpropyl)chromium(III). This compound was dissolved in distillation-purified hexane to obtain a solution of 0.10 mol/liter, 5.20 g/liter. ) were reacted to obtain a solution of 0.10 mol/liter, 5.20 g/liter

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The known but unavailable 2,2-dimethylpropyl diphenyl phosphine was derived via reacting 2,2-dimethylpropyl chloride with lithium diphenyl phosphide in a refluxing tetrahydrofuran-hexane solvent mixture. After filtering off the lithium chloride by-product, the 2,2-dimethylpropyl, (i.e., neopentyl) diphenyl phosphine was obtained by the fractional distillation of the filtrate between 109° and 110° C. at 0.1 mm. After filtering off the lithium chloride by-product

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The known but unavailable 2,2-dimethylpropyl diphenyl phosphine was derived via reacting 2,2-dimethylpropyl chloride with lithium diphenyl phosphide in a refluxing tetrahydrofuran-hexane solvent mixture. After filtering off the lithium chloride by-product, the 2,2-dimethylpropyl, (i.e., neopentyl) diphenyl phosphine was obtained by the fractional distillation of the filtrate between 109° and 110° C. at 0.1 mm. After filtering off the lithium chloride by-product

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of p,p'-di-t-butyl biphenyl (5.559 g, 0.021 mol) and THF (100 mL) was stirred at 0° C. under an atmosphere of argon. Lithium wire (0.021 mol, 0.15 g) was added in small pieces and the mixture was allowed to stir at 0° C. for 24 h. The mixture was cooled to -78° C. and neopentyl chloride (2.0 g, 0.01875 mol) was added dropwise. The mixture was stirred at -78° C. for 1 h, and the compound of Example g (3.17 g, 0.015 mol) was added all at once. The mixture was continuously stirred for 4 h and 50 mL sat aq NaHCO3 was added. This mixture was extracted with three 50 mL portions of ethyl acetate. The combined extracts were washed twice with water, dried (MgSO4), and concentrated. The crude concentrate was purified by HPLC eluting with 1:4 ethyl acetate/hexanes. The oxazoline was as a clear oil in 27% yield. The mixture was cooled to -78° C. The mixture was stirred at -78° C. for 1 h The mixture was continuously stirred for 4 h was added This mixture was extracted with three 50 mL portions of ethyl acetate The combined extracts were washed twice with water dried (MgSO4) concentrated The crude concentrate was purified by HPLC eluting with 1:4 ethyl acetate/hexanes

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of p,p'-di-t-butyl biphenyl (5.559 g, 0.021 mol) and THF (100 mL) was stirred at 0° C. under an atmosphere of argon. Lithium wire (0.021 mol, 0.15 g) was added in small pieces and the mixture was allowed to stir at 0° C. for 24 h. The mixture was cooled to -78° C. and neopentyl chloride (2.0 g, 0.01875 mol) was added dropwise. The mixture was stirred at -78° C. for 1 h, and the compound of Example g (3.17 g, 0.015 mol) was added all at once. The mixture was continuously stirred or 4 h and 50 mL sat aq NaHCO3 was added. This mixture as extracted with three 50 mL portions of ethyl acetate. The combined extracts were washed twice with water, dried (MgSO4), and concentrated. The crude concentrate was purified by HPLC eluting with 1:4 ethyl acetate/hexanes. The oxazoline was as a clear oil in 27% yield. The mixture was cooled to -78° C. The mixture was stirred at -78° C. for 1 h The mixture was continuously stirred or 4 h was added This mixture as extracted with three 50 mL portions of ethyl acetate The combined extracts were washed twice with water dried (MgSO4) concentrated The crude concentrate was purified by HPLC eluting with 1:4 ethyl acetate/hexanes

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of p,p'-di-t-butyl biphenyl (5.559 g, 0.021 mol) and THF (100 mL) was stirred at 0° C. under an atmosphere of argon. Lithium wire (0.021 mol, 0.15 g) was added in small pieces and the mixture was allowed to stir at 0° C. for 24 h. The mixture was cooled to -78° C. and neopentyl chloride (2.0 g, 0.01875 mol) was added dropwise. The mixture was stirred at -78° C. for 1 h, and the compound of Example g (3.17 g, 0.015 mol) was added all at once. The mixture was continuously stirred for 4 h and 50 mL sat aq NaHCO3 was added. This mixture was extracted with three 50 mL portions of ethyl acetate. The combined extracts were washed twice with water, dried (MgSO4), and concentrated. The crude concentrate was purified by HPLC eluting with 1:4 ethyl acetate/hexanes. The oxazoline was as a clear oil in 27% yield. The mixture was cooled to -78° C. The mixture was stirred at -78° C. for 1 h The mixture was continuously stirred for 4 h was added This mixture was extracted with three 50 mL portions of ethyl acetate The combined extracts were washed twice with water dried (MgSO4) concentrated The crude concentrate was purified by HPLC eluting with 1:4 ethyl acetate/hexanes

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of p,p'-di-t-butyl biphenyl (5.559 g, 0.021 mol) and THF (100 mL) was stirred at 0° C. under an atmosphere of argon. Lithium wire (0.021 mol, 0.15 g) was added in small pieces and the mixture was allowed to stir at 0° C. for 24 h. The mixture was cooled to -78° C. and neopentyl chloride (2.0 g, 0.01875 mol) was added dropwise. The mixture was stirred at -78° C. for 1 h, and the compound of Example g (3.17 g, 0.015 mol) was added all at once. The mixture was continuously stirred for 4 h and 50 mL sat aq NaHCO3 was added. This mixture was extracted with three 50 mL portions of ethyl acetate. The combined extracts were washed twice with water, dried (MgSO4), and concentrated. The crude concentrate was purified by HPLC eluting with 1:4 ethyl acetate/hexanes. The oxazoline was as a clear oil in 27% yield. The mixture was cooled to -78° C. The mixture was stirred at -78° C. for 1 h The mixture was continuously stirred for 4 h was added This mixture was extracted with three 50 mL portions of ethyl acetate The combined extracts were washed twice with water dried (MgSO4) concentrated The crude concentrate was purified by HPLC eluting with 1:4 ethyl acetate/hexanes

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of p,p'-di-t-butyl biphenyl (5.559 g, 0.021 mol) and THF (100 mL) was stirred at 0° C. under an atmosphere of argon. Lithium wire (0.021 mol, 0.15 g) was added in small pieces and the mixture was allowed to stir at 0° C. for 24 h. The mixture was cooled to -78° C. and neopentyl chloride (2.0 g, 0.01875 mol) was added dropwise. The mixture was stirred at -78° C. for 1 h, and the compound of Example g (3.17 g, 0.015 mol) was added all at once. The mixture was continuously stirred or 4 h and 50 mL sat aq NaHCO3 was added. This mixture as extracted with three 50 mL portions of ethyl acetate. The combined extracts were washed twice with water, dried (MgSO4), and concentrated. The crude concentrate was purified by HPLC eluting with 1:4 ethyl acetate/hexanes. The oxazoline was as a clear oil in 27% yield. The mixture was cooled to -78° C. The mixture was stirred at -78° C. for 1 h The mixture was continuously stirred or 4 h was added This mixture as extracted with three 50 mL portions of ethyl acetate The combined extracts were washed twice with water dried (MgSO4) concentrated The crude concentrate was purified by HPLC eluting with 1:4 ethyl acetate/hexanes

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Mix magnesium turnings (45 mg, 1.85 mmol) and 1-chloro-2,2-dimethylpropane (74.6 mg, 0.7 mmol) in anhydrous ether (9 mL). Heat and stir vigorously, then add, by dropwise addition, 1,2-dibromoethane (156 mg, 0.839 mmol) in anhydrous ether (1.5 mL). Reflux for 12 hours, place under an argon atmosphere and cool to 0°-5° C. Add, by dropwise addition, a solution of isobutyryl chloride (0.533 mmol) in anhydrous diethyl ether (1.5 mL). Stir at 0°-5° C. for 1.5 hours, pour into a mixture of ice and concentrated hydrochloric acid (0.15 mL) and separate the organic phase. Wash with ethyl acetate, 5% aqueous sodium carbonate and brine. Dry (MgSO4) and evaporate the solvent in vacuo to give 2,2,6-trimethyl-4-heptanone. Heat Reflux for 12 hours place under an argon atmosphere and cool to 0°-5° C Add, by dropwise addition Stir at 0°-5° C. for 1.5 hours separate the organic phase Wash with ethyl acetate, 5% aqueous sodium carbonate and brine Dry (MgSO4) evaporate the solvent in vacuo