Acetone → HCID 86628873, compound

HRID 1671413Notes

Reaction equation

[Cl:1][CH2:2][CH2:3][CH2:4][S:5]([O:8][CH2:9][C:10]([CH3:25])([CH3:24])[C@@H: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])[C@@H: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

Reactant 2

HCID 180Acetone

HCID 86628871HCID 86628871, compound

Product 1

HCID 86628873HCID 86628873, compoundYield 96%

Procedure

Following the general procedure for the oxidation of aldehydes to carboxylic acids of Description 13, (3R)-3-[(4-methoxyphenyl)methoxy]-2,2-dimethyl-4-oxobutyl (3-chloropropyl)sulfonate (13b) (2.0 g, 5.1 mmol) dissolved in 30 mL of acetone was reacted with 2.6 mL of Jones-reagent (2.0 M in water). After work-up, 2.0 g (96% yield) of the title compound (13) was obtained as a colorless oil. 1H NMR (400 MHz, CDCl3): δ=1.09 (s, 3H), 1.10 (s, 3H), 2.28-2.35 (m, 2H), 3.27-3.31 (m, 2H), 3.66-3.69 (m, 2H), 3.82 (s, 3H), 3.88 (s, 1H), 4.02 (d, J=9.2 Hz, 1H), 4.19 (d, J=9.2 Hz, 1H), 4.45 (d, J=10.8 Hz, 1H), 4.60 (d, J=10.8 Hz, 1H), 6.90 (d, J=8.8 Hz, 2H), 7.28 (d, J=8.8 Hz, 2H) ppm. MS (ESI) m/z 430.90 (M+Na)+. The analytical data was consistent with the proposed structure.

Workup

customwas reacted with 2.6 mL of Jones-reagent (2.0 M in water)

Sources & evidence

ORD record: ord-0bf8947f35244f59bce27418f46dde7e
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07994218B2

Reaction notes

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