Potassium Carbonate → 6-{[tert-Butyl(dimethyl)silyl]oxy}hexanoic acid

HRID 1638182Notes

Reaction equation

HRID 1638182 reaction equation
[SiH3][O:2][C:3](=[O:17])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].C([O-])([O-])=O.[K+].[K+].OS([O-])(=O)=O.[K+]>CO.O.[Na+].[Cl-]>[Si:10]([O:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:17])=[O:2])([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 516920Potassium bisulfateHCID 123778939HCID 123778939, compound

Product 1

HCID 127173116-{[tert-Butyl(dimethyl)silyl]oxy}hexanoic acidYield 90%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 5234Sodium ChlorideSolvent

Procedure

A solution of 3.25 g (9.02 mmol) of the bissilylated compound 6-[(tert-butyldimethyl-silyl)oxy]-hexanoic acid silyl ester in 130 ml of methanol and 44 ml of ThF is mixed with a solution of 4.4 g (31.8 mmol, 3.5 equivalents) of K2CO3 in 44 ml of H2O, and it is stirred for 1 hour at room temperature. Then, the volume of reaction solution is reduced to one-fourth in a vacuum. It is diluted with 130 ml of saturated NaCl solution and set at pH 4-5 with 1 M KHSO4 solution. It is extracted with diethyl ether. The combined organic phases are dried on MgSO4, and the solvent is distilled off in a rotary evaporator. 2.01 g (8.17 mmol) of 6-[(tert-butyldimethylsilyl)oxy]-hexanoic acid, corresponding to a yield of 90%, is obtained.

Workup

  1. customThen, the volume of reaction solution
  2. extractionIt is extracted with diethyl ether
  3. customThe combined organic phases are dried on MgSO4
  4. distillationthe solvent is distilled off in a rotary evaporator

Sources & evidence

ORD record
ord-63e77efa55564e7bbfa53fa33c36d75d
Source dataset
uspto-grants-2000_03
Patent number
US06043372

Reaction notes

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