3,3,4-trimethylpentan-1-ol

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

Procedure: 3,3,4-Trimethylpentanol (1 equiv) is dissolved in CH2Cl2. Pyridinium chlorochromate (1.5 equiv) is added and the resulting mixture is stirred at ambient temperature. The liquid is decanted and concentrated by rotary evaporation. The residue is triturated with 1 to 1 diethyl ether/hexane and mixture is filtered and the filtrate is washed with 1 N HCl. The organic layer is dried over Na2SO4, decanted and concentrated. The aldehyde is purified by fractional distillation to yield 3,3,4-trimethylpentanal. The liquid is decanted concentrated by rotary evaporation The residue is triturated with 1 to 1 diethyl ether/hexane and mixture is filtered the filtrate is washed with 1 N HCl The organic layer is dried over Na2SO4 decanted concentrated The aldehyde is purified by fractional distillation

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

Procedure: 3,3,4-Trimethylpentene (1 equiv) is dissolved in dry THF under Ar. The reaction mixture is cooled to −78° C. at which time a 1 M solution of borane/dimethylsulfide complex in THF (0.4 equiv) is added dropwise. The cold bath is removed and the reaction mixture is allowed to warm to ambient temperature. The reaction mixture is carefully diluted with a solution of sodium acetate in aqueous hydrogen peroxide (large exess). The reaction mixture is stirred at ambient temperature and then diluted with diethyl ether and the layers are separated. The organic layer is dried over Na2SO4, decanted and concentrated. The crude material is purified by fractional distillation to yield 3,3,4-trimethylpentanol. is added dropwise The cold bath is removed The reaction mixture is carefully diluted with a solution of sodium acetate in aqueous hydrogen peroxide (large exess) diluted with diethyl ether the layers are separated The organic layer is dried over Na2SO4 decanted concentrated The crude material is purified by fractional distillation

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

Procedure: 3,3,4-Trimethylpentene (1 equiv) is dissolved in dry THF under Ar. The reaction mixture is cooled to −78° C. at which time a 1 M solution of borane/dimethylsulfide complex in THF (0.4 equiv) is added dropwise. The cold bath is removed and the reaction mixture is allowed to warm to ambient temperature. The reaction mixture is carefully diluted with a solution of sodium acetate in aqueous hydrogen peroxide (large exess). The reaction mixture is stirred at ambient temperature and then diluted with diethyl ether and the layers are separated. The organic layer is dried over Na2SO4, decanted and concentrated. The crude material is purified by fractional distillation to yield 3,3,4-trimethylpentanol. is added dropwise The cold bath is removed The reaction mixture is carefully diluted with a solution of sodium acetate in aqueous hydrogen peroxide (large exess) diluted with diethyl ether the layers are separated The organic layer is dried over Na2SO4 decanted concentrated The crude material is purified by fractional distillation

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

Procedure: Step C To a solution of 3,3,4-trimethyl-pentan-1-ol (5.4 g, 41 mmol) in dichloromethane (100 mL) was added Dess-Martin periodinane (22 g 52 mmol) The reaction mixture was stirred at room temperature for 3 h. Aqueous Na2SO3 solution was added to quench the reaction. The organic layers were separated, washed with saturated NaHCO3, brine, dried over MgSO4, and concentrated. The residue was purified by chromatography (EtOAc:hexanes=1:30) to give 3,3,4-trimethyl-pentanal as a colorless oil (Yield: 1.1 g, 21%). to quench the reaction The organic layers were separated washed with saturated NaHCO3, brine dried over MgSO4 concentrated The residue was purified by chromatography (EtOAc:hexanes=1:30)

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

Procedure: Step B To a solution of 3,3,4-trimethyl-pentanoic acid ethyl ester (7 g, 41 mmol) in anhydrous ethyl ether (100 mL) at 0° C. was added a ethyl ether solution (1 M) of LiAlH4 (67 mL, 67 mmol) under nitrogen. The reaction mixture was stirred at 0° C. for 1 h, then poured into a ice-water. The mixture was extracted with ethyl acetate. The organic layer were separated, washed with water, aqueous HCl solution, brine, dried over MgSO4, and concentrated to give 3,3,4-trimethyl-pentan-1-ol as a colorless oil (5.4 g, 100%). The mixture was extracted with ethyl acetate The organic layer were separated washed with water, aqueous HCl solution, brine dried over MgSO4 concentrated

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

Procedure: 3,3,4-Trimethylpentanol (1 equiv) is dissolved in CH2Cl2. Pyridinium chlorochromate (1.5 equiv) is added and the resulting mixture is stirred at ambient temperature. The liquid is decanted and concentrated by rotary evaporation. The residue is triturated with 1 to 1 diethyl ether/hexane and mixture is filtered and the filtrate is washed with 1 N HCl. The organic layer is dried over Na2SO4, decanted and concentrated. The aldehyde is purified by fractional distillation to yield 3,3,4-trimethylpentanal. The liquid is decanted concentrated by rotary evaporation The residue is triturated with 1 to 1 diethyl ether/hexane and mixture is filtered the filtrate is washed with 1 N HCl The organic layer is dried over Na2SO4 decanted concentrated The aldehyde is purified by fractional distillation

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

Procedure: 3,3,4-Trimethylpentene (1 equiv) is dissolved in dry THF under Ar. The reaction mixture is cooled to −78° C. at which time a 1 M solution of borane/dimethylsulfide complex in THF (0.4 equiv) is added dropwise. The cold bath is removed and the reaction mixture is allowed to warm to ambient temperature. The reaction mixture is carefully diluted with a solution of sodium acetate in aqueous hydrogen peroxide (large exess). The reaction mixture is stirred at ambient temperature and then diluted with diethyl ether and the layers are separated. The organic layer is dried over Na2SO4, decanted and concentrated. The crude material is purified by fractional distillation to yield 3,3,4-trimethylpentanol. is added dropwise The cold bath is removed The reaction mixture is carefully diluted with a solution of sodium acetate in aqueous hydrogen peroxide (large exess) diluted with diethyl ether the layers are separated The organic layer is dried over Na2SO4 decanted concentrated The crude material is purified by fractional distillation