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

HRID 514464Notes

Reaction equation

HRID 514464 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-f5a605304d5f458eaca8a8ebc79e3d17
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Reaction notes

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