Acetone → (2R)-4-[(3-Chloropropyl)sulfonyloxy]-3,3-dimethyl-2-(1,1,2,2-tetramethyl-1-silapropoxy)butanoic acid

HRID 1919411Notes

Reaction equation

HRID 1919411 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][S:5]([O:8][CH2:9][C:10]([CH3:23])([CH3:22])[C@@H:11]([O:14][Si:15]([CH3:21])([CH3:20])[C:16]([CH3:19])([CH3:18])[CH3:17])[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])[C@@H:11]([O:14][Si:15]([CH3:21])([CH3:20])[C:16]([CH3:18])([CH3:17])[CH3:19])[C:12]([OH:26])=[O:13])(=[O:7])=[O:6]

Participants

3

Reactant 2

HCID 180AcetoneHCID 86628875(3R)-2,2-Dimethyl-4-oxo-3-(1,1,2,2-tetramethyl-1-silapropoxy)butyl (3-chloropropyl)sulfonate

Product 1

HCID 86628876(2R)-4-[(3-Chloropropyl)sulfonyloxy]-3,3-dimethyl-2-(1,1,2,2-tetramethyl-1-silapropoxy)butanoic acidYield 79%

Procedure

Following the general procedure of the oxidation of aldehydes to carboxylic acids of Description 13, (3R)-2,2-dimethyl-4-oxo-3-(1,1,2,2-tetramethyl-1-silapropoxy)butyl (3-chloropropyl)sulfonate (15b) (1.1 g, 2.8 mmol) dissolved in 20 mL of acetone was reacted with 1.4 mL of Jones-reagent (2.0 M in water). After work-up, 0.9 g (79% yield) of the title compound (15) was obtained as a colorless oil. 1H NMR (400 MHz, CDCl3): δ=0.13 (s, 3H), 0.16 (s, 3H), 0.98 (s, 9H), 1.05 (s, 3H), 1.11 (s, 3H), 2.32-2.39 (m, 2H), 3.33-3.36 (m, 2H), 3.69-3.72 (m, 2H), 4.04 (d, J=9.6 Hz, 1H), 4.09 (s, 1H), 4.12 (d, J=9.6 Hz, 1H) ppm. MS (ESI) m/z 403.00 (M+H)+; 401.05 (M−H)−. The analytical data was consistent with the proposed structure.

Workup

  1. customwas reacted with 1.4 mL of Jones-reagent (2.0 M in water)

Sources & evidence

ORD record
ord-fb17765a2f0243c884ea03b95ed53b2f
Source dataset
uspto-grants-2012_05
Patent number
US08168617B2

Reaction notes

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