Acetone → (2R/S)-4-[(3-Chloropropyl)sulfonyloxy]-3,3-dimethyl-2-(phenylmethoxy)butanoic acid

HRID 1671411Notes

Reaction equation

HRID 1671411 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][S:5]([O:8][CH2:9][C:10]([CH3:23])([CH3:22])[CH:11]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:12]=[O:13])(=[O:7])=[O:6].CC(C)=[O:26]>>[Cl:1][CH2:2][CH2:3][CH2:4][S:5]([O:8][CH2:9][C:10]([CH3:23])([CH3:22])[CH:11]([O:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:12]([OH:26])=[O:13])(=[O:7])=[O:6]

Participants

3

Reactant 2

HCID 180AcetoneHCID 131729094(3r/s)-2,2-Dimethyl-4-oxo-3-(phenylmethoxy)butyl (3-chloropropyl)sulfonate

Product 1

HCID 87453922(2R/S)-4-[(3-Chloropropyl)sulfonyloxy]-3,3-dimethyl-2-(phenylmethoxy)butanoic acidYield 96%

Procedure

Following the general procedure of the oxidation of aldehydes to carboxylic acids of Description 13, (3R/S)-2,2-dimethyl-4-oxo-3-(phenylmethoxy)butyl (3-chloropropyl)sulfonate (12b) (7.6 g, 21 mmol) dissolved in 100 mL of acetone was reacted with 10.5 mL of Jones-reagent (2.0 M in water). After work-up, 7.6 g (96% yield) of the title compound (12) was obtained as a colorless oil. The analytical data was consistent with the proposed structure and the data obtained for the enantiopure compound (11).

Workup

  1. customwas reacted with 10.5 mL of Jones-reagent (2.0 M in water)

Sources & evidence

ORD record
ord-59746aa775af4ba88cc6c148f0fceefd
Source dataset
uspto-grants-2011_08
Patent number
US07994218B2

Reaction notes

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