1,1-Dimethoxyethyl(dimethyl)amine → HCID 117737325, compound

HRID 1504380Notes

Reaction equation

HRID 1504380 reaction equation
[CH2:1]([S:8][C:9]1[CH:10]=[CH:11][C:12]([F:18])=[C:13]([C:15](=[O:17])[CH3:16])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[C:21](OC)([N:23]([CH3:25])[CH3:24])[CH3:22]>>[CH2:1]([S:8][C:9]1[CH:10]=[CH:11][C:12]([F:18])=[C:13]([C:15](=[O:17])/[CH:16]=[C:21](/[N:23]([CH3:25])[CH3:24])\[CH3:22])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 117737202HCID 117737202, compound

Product 1

HCID 117737325HCID 117737325, compoundYield 63.7%

Procedure

A solution of 1-(5-(benzylthio)-2-fluorophenyl)ethanone (3.6 g, 13.83 mmol) in N,N-dimethylacetamide dimethyl acetal (12.13 mL, 83 mmol) was irradiated at 130° C. for 10 minutes in a microwave reactor (Biotage Initiator). The reaction mixture was partitioned between water and ethyl acetate, and the organic layer was concentrated. The crude product was purified by column chromatography, eluting with 20-100% ethyl acetate in heptane, to provide (E)-1-(5-(benzylthio)-2-fluorophenyl)-3-(dimethylamino)but-2-en-1-one (2.9 g, 8.80 mmol, 63.7% yield) as a tan solid. m/z (ESI) 330.0 (M+H).

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. concentrationthe organic layer was concentrated
  3. customThe crude product was purified by column chromatography
  4. washeluting with 20-100% ethyl acetate in heptane

Sources & evidence

ORD record
ord-98e078cd17cb493891b39c75480ad14c
Source dataset
uspto-grants-2015_12
Patent number
US09212182B2

Reaction notes

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