Potassium bisulfate → 4-{[tert-Butyl(dimethyl)silyl]oxy}butanoic acid

HRID 878621Notes

Reaction equation

HRID 878621 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][Li])=[O:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].OS([O-])(=O)=O.[K+]>C(OCC)(=O)C>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 516920Potassium bisulfateHCID 178506949HCID 178506949, compound

Product 1

HCID 1868234-{[tert-Butyl(dimethyl)silyl]oxy}butanoic acidYield 95%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-[tert-butyl(dimethyl)silyl]oxybutanoyloxylithium (8.0 g, 35.71 mmol) in ethyl acetate (10 mL), was carefully added KHSO4 (5%) to adjust pH to about 1. It was then extracted with ethyl acetate three times and organic extracts washed with brine and dried with anhydrous NaSO4. The organic extracts were concentrated to give the title compound (7.4 g, 95%). [M+H] Calc'd for C10H22O3Si, 219; Found, 219.

Workup

  1. extractionIt was then extracted with ethyl acetate three times and organic extracts
  2. washwashed with brine
  3. dry with materialdried with anhydrous NaSO4
  4. concentrationThe organic extracts were concentrated

Sources & evidence

ORD record
ord-6031e919e9a34a09947d5a51c04406eb
Source dataset
uspto-grants-2015_03
Patent number
US08987461B2

Reaction notes

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