Acetic Acid → 1-(3-Benzyloxyphenyl)-3-(3-(methoxycarbonyl)phenyl)-2-propen-1-one

HRID 6375

反応式

HRID 6375 の反応式
CO[Na].[CH3:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:8]=1)=[O:6].[CH:21]([C:23]1[CH:24]=[C:25]([CH:30]=[CH:31][CH:32]=1)[C:26]([O:28][CH3:29])=[O:27])=O.C(O)(=O)C>CO.O>[CH2:14]([O:13][C:9]1[CH:8]=[C:7]([C:5](=[O:6])[CH:4]=[CH:21][C:23]2[CH:32]=[CH:31][CH:30]=[C:25]([C:26]([O:28][CH3:29])=[O:27])[CH:24]=2)[CH:12]=[CH:11][CH:10]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

7

反応物 4

HCID 176Acetic AcidHCID 986891-(3-(Phenylmethoxy)phenyl)ethan-1-oneHCID 639145Methyl 3-formylbenzoateHCID 178418582HCID 178418582、化合物

生成物 1

HCID 536734501-(3-Benzyloxyphenyl)-3-(3-(methoxycarbonyl)phenyl)-2-propen-1-one

試薬・触媒・溶媒 2

HCID 887Methanol溶媒2 回HCID 962Water溶媒

実験手順

To CH3ONa (0.45 g, 0.0082 mol) stirring in 20 ml of dry CH3OH at 10° C. was added 3-benzyloxyacetophenone (5.0 g, 0.019 mol) and methyl 3-formylbenzoate (3.12 g, 0.019 mol). A heavy precipitate formed almost immediately, and the mixture was diluted with 20 ml CH3OH, warmed to room temperature and stirred for 18 hours. Glacial acetic acid (3 ml) was added and the mixture poured into 300 ml H2O. Title product was recovered by filtration, air dried and purified by chromatography on silica gel gradiently eluted with 49 to 39:1 toluene:ethyl acetate, 4.97 g of solid; MS 372.2 (M+); 1H-NMR (300 MHz, CDCl3) delta (ppm) 3.95 (s, 3H), 5.14 (s, 2H), 7.2-7.9 (m, 13H), 8.06 (dt, 1H), 8.3 (s, 1H); TLC Rf 0.7 (49:1 CHCl3 :isopropanol).

後処理

  1. customA heavy precipitate formed almost immediately
  2. filtrationTitle product was recovered by filtration, air
  3. customdried
  4. custompurified by chromatography on silica gel
  5. washgradiently eluted with 49 to 39:1 toluene

出典と根拠

ORDレコード
ord-02e63018c7f6403a9ad3b2d6de31b313
出典データセット
uspto-grants-1993_09
特許番号
US05248685

関連ノート

読み込み中…