3-Hydroxyacetophenone → HCID 69517765, compound

HRID 1581784Notes

Reaction equation

[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([OH:10])[CH:9]=1)=[O:3].CO[CH:13](OC)[N:14]([CH3:16])[CH3:15]>>[CH3:13][N:14]([CH3:16])[CH:15]=[CH:1][C:2]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([OH:10])[CH:9]=1)=[O:3]

Participants

Reactant 2

HCID 84873-Hydroxyacetophenone

HCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 69517765HCID 69517765, compoundYield 37%

Conditions

Temperature: 100 °C

Procedure

A mixture of 3-hydroxyacetophenone (20.0 g, 146.9 mmol) and N,N-dimethylformamide dimethyl acetal (26.26 g, 220.4 mmol) is heated over night at 100° C. The excess of the acetal is removed under reduced pressure and 3-(dimethylamino)-1-(3-hydroxyphenyl)-2-propen-1-one (10.32 g, 37%) is obtained after chromatography on silica gel with dichloromethane/ethanol 9:1. This intermediate enone is reacted with (2S)-glycidyl 3-nitrobenzenesulfonate substantially as described for Epoxide 1 to give 5.02 g of the title epoxide (78%).

Workup

customThe excess of the acetal is removed under reduced pressure

Sources & evidence

ORD record: ord-4730904199674c0d98f8a658d53fc01c
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06730792B2

Reaction notes

Loading…