3,3-dimethylbutan-2-ol

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A mixture of 3 mmol of methyl acrylate, 15 mmol of 3,3-dimethyl-2-butanol, 0.3 mmol of N-hydroxyphthalimide, 0.003 mmol of cobalt(II) acetate, 0.03 mmol of acetylacetonatocobalt(III), and 1 ml of acetonitrile was stirred at 50° C. in an oxygen atmosphere (1 atm) for 5 hours. A reaction mixture was subjected to column chromatography on a silica gel to yield 3-hydroxy-2-oxo-1-oxaspiro[4.5]decane in a yield of 83%.

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

Procedure: A mixture of 3 mmol of methyl acrylate, 15 mmol of 3,3-dimethyl-2-butanol, 0.6 mmol of N-hydroxyphthalimide, 0.003 mmol of cobalt(II) acetate, 0.03 mmol of acetylacetonatocobalt(III), and 1 ml of acetonitrile was stirred at 60° C. in an oxygen atmosphere (1 atm) for 8 hours. A reaction mixture was subjected to column chromatography on a silica gel to yield γ-t-butyl-α-hydroxy-γ-methyl-γ-butyrolactone in a yield of 71%.

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

Procedure: A mixture of 3 mmol of methyl acrylate, 15 mmol of 3,3-dimethyl-2-butanol, 0.3 mmol of N-hydroxyphthalimide, 0.003 mmol of cobalt(II) acetate, 0.03 mmol of acetylacetonatocobalt(III), and 1 ml of acetonitrile was stirred at 50° C. in an oxygen atmosphere (1 atm) for 5 hours. A reaction mixture was subjected to column chromatography on a silica gel to yield 3-hydroxy-2-oxo-1-oxaspiro[4.5]decane in a yield of 83%.

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

Procedure: A mixture of 3 mmol of methyl acrylate, 15 mmol of 3,3-dimethyl-2-butanol, 0.6 mmol of N-hydroxyphthalimide, 0.003 mmol of cobalt(II) acetate, 0.03 mmol of acetylacetonatocobalt(III), and 1 ml of acetonitrile was stirred at 60° C. in an oxygen atmosphere (1 atm) for 8 hours. A reaction mixture was subjected to column chromatography on a silica gel to yield γ-t-butyl-α-hydroxy-γ-methyl-γ-butyrolactone in a yield of 71%.

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3,3-dimethylbutan-2-ol (0.18 mL) in toluene (4 mL) was added sodium hydride (0.14 g), and the resulting mixture was stirred at 70° C. for 15 min under a nitrogen atmosphere. A mixture of tert-butyl 8-chloro-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate (0.50 g), BINAP (0.033 g), Pd2(dba)3 (0.024 g) and toluene (4 mL) was added, and the resulting mixture was stirred at 100° C. for 2 hr under an argon atmosphere. The reaction solution was poured into water, and the resulting product was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (solvent gradient; 0→40% ethyl acetate/hexane) to give tert-butyl 8-(1,2,2-trimethylpropoxy)-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate (0.38 g, 62%) as a white powder. was added the resulting mixture was stirred at 100° C. for 2 hr under an argon atmosphere the resulting product was extracted with ethyl acetate The organic layer was washed with water and saturated brine dried the solvent was evaporated under reduced pressure The residue was purified by silica gel column chromatography (solvent gradient; 0→40% ethyl acetate/hexane)

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

Procedure: 47.5 g (0.42 mole) of chloracetyl chloride was slowly added to a mixture of 40.9 g (0.4 mole) of 3,3-dimethyl 2-butanol and 58 ml (0.42 mole) of triethylamine. The reaction mixture kept at 10° C. during the running in of the acid chloride, was brought to ordinary temperature and stirred for about 4 hours. After filtration and washing with ether of triethylamine hydrochloride, the solution was washed with water then dried over sodium sulfate. After evaporation of the solvent and distillation of the vacuum, 64 g namely 89% was obtained of a pure liquid of b.p.t =79°/81° C. under 20 mm Hg. kept at 10° C. After filtration washing with ether of triethylamine hydrochloride the solution was washed with water then dried over sodium sulfate After evaporation of the solvent and distillation of the vacuum, 64 g namely 89% was obtained of a pure liquid of b.p.t =79°/81° C. under 20 mm Hg

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

Procedure: In 4 ml of tetrahydrofuran was suspended 0.11 g of sodium hydride (60% in oil), to which 0.5 ml of tetrahydrofuran containing 0.23 g of 3,3-dimethyl-2-butanol dissolved therein was added dropwise at room temperature, followed by stirring for 10 minutes. To this was added dropwise 0.5 ml of tetrahydrofuran containing 0.3 g of 4,6-dichloropyrimidine dissolved therein, followed by stirring at the same temperature for 6 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.24 g of 4-chloro-6-(1,2,2-trimethylpropyloxy)pyrimidine. therein was added dropwise at room temperature dissolved by stirring at the same temperature for 6 hours was extracted three times with t-butyl methyl ether The combined organic layers were washed with a saturated aqueous sodium chloride solution dried over anhydrous magnesium sulfate concentrated

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

Procedure: A mixture of 3 mmol of methyl acrylate, 15 mmol of 3,3-dimethyl-2-butanol, 0.3 mmol of N-hydroxyphthalimide, 0.003 mmol of cobalt(II) acetate, 0.03 mmol of acetylacetonatocobalt(III), and 1 ml of acetonitrile was stirred at 50° C. in an oxygen atmosphere (1 atm) for 5 hours. A reaction mixture was subjected to column chromatography on a silica gel to yield 3-hydroxy-2-oxo-1-oxaspiro[4.5]decane in a yield of 83%.

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

Procedure: A mixture of 3 mmol of methyl acrylate, 15 mmol of 3,3-dimethyl-2-butanol, 0.6 mmol of N-hydroxyphthalimide, 0.003 mmol of cobalt(II) acetate, 0.03 mmol of acetylacetonatocobalt(III), and 1 ml of acetonitrile was stirred at 60° C. in an oxygen atmosphere (1 atm) for 8 hours. A reaction mixture was subjected to column chromatography on a silica gel to yield γ-t-butyl-α-hydroxy-γ-methyl-γ-butyrolactone in a yield of 71%.