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

HRID 1740480Notes

Reaction equation

HRID 1740480 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-a1fb7c42c69c4b33b2ca17b49f2b081d
Source dataset
uspto-grants-1999_10
Patent number
US05969145

Reaction notes

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