Acetone → HCID 87601326, compound

HRID 1919408Notes

Reaction equation

HRID 1919408 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][S:5]([O:8][CH2:9][C:10]([CH3:25])([CH3:24])[CH:11]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)[CH:12]=[O:13])(=[O:7])=[O:6].CC(C)=[O:28]>>[Cl:1][CH2:2][CH2:3][CH2:4][S:5]([O:8][CH2:9][C:10]([CH3:25])([CH3:24])[CH:11]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)[C:12]([OH:28])=[O:13])(=[O:7])=[O:6]

Participants

3

Reactant 2

HCID 180AcetoneHCID 131729096HCID 131729096, compound

Product 1

HCID 87601326HCID 87601326, compoundYield 87%

Procedure

Following the general procedure of the oxidation of aldehydes to carboxylic acids of Description 13, (3R/S)-3-[(4-methoxyphenyl)methoxy]-2,2-dimethyl-4-oxobutyl (3-chloropropyl)sulfonate (14b) (3.1 g, 7.9 mmol) dissolved in 40 mL of acetone was reacted with 3.9 mL of Jones-reagent (2.0 M in water). After work-up, 2.8 g (87% yield) of the title compound (14) was obtained as a colorless oil. The analytical data was consistent with the proposed structure and with the data obtained for the enantiopure compound (13).

Workup

  1. customwas reacted with 3.9 mL of Jones-reagent (2.0 M in water)

Sources & evidence

ORD record
ord-9d55d194935140eaba3ee064e367134d
Source dataset
uspto-grants-2012_05
Patent number
US08168617B2

Reaction notes

Loading…