Dimethylformamide dimethyl acetal → HCID 57732419, compound

HRID 1365066Notes

Reaction equation

HRID 1365066 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[CH:11]([OH:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CO[CH:21](OC)[N:22]([CH3:24])[CH3:23]>>[CH3:21][N:22]([CH3:24])/[CH:23]=[CH:9]/[C:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([CH:11]([OH:18])[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:4]=1)=[O:10]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 577324311-[4-Fluoro-3-(hydroxyphenylmethyl)phenyl]ethanone

Product 1

HCID 57732419HCID 57732419, compound

Procedure

A round-bottomed flask was charged with 1-{4-fluoro-3-[hydroxy(phenyl)methyl]phenyl}ethanone (140 mg) and dimethylformamide dimethylacetal (4 mL). The mixture was heated to reflux for 18 h then concentrated to dryness. The residue was taken up in minimal methylene chloride then added to rapidly stirring diethyl ether to induce a solid. The solids were collected on filter and washed with diethyl ether to provide (2E)-3-(dimethylamino)-1-{4-fluoro-3-[hydroxy(phenyl)methyl]phenyl}-2-propen-1-one as a white powder (60 mg). 8.09 (dd, 1H), 7.82 (m, 1H), 7.69 (d, 1H), 7.31 (m, 4H), 7.21 (m, 1H), 7.14 (dd, 1H), 6.06 (d, 1H), 5.94 (d, 1H), 5.75 (d, 1H), 3.14 (s, 3H), 2.88 (s, 3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 18 h
  3. concentrationthen concentrated to dryness
  4. additionthen added to rapidly stirring diethyl ether
  5. customThe solids were collected
  6. filtrationon filter
  7. washwashed with diethyl ether

Sources & evidence

ORD record
ord-739cc7860f1b4969ac9766ee7c136ecf
Source dataset
uspto-grants-2011_02
Patent number
US07888503B2

Reaction notes

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