Water → Methyl 2-(2'-benzyloxyphenyl)-3-hydroxyacrylate

HRID 345272ノート

反応式

HRID 345272 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][C:16]([O:18][CH3:19])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:20](OC)=[O:21].[H-].[Na+].O>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15](=[CH:20][OH:21])[C:16]([O:18][CH3:19])=[O:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 962WaterHCID 7865Methyl formateHCID 24758Sodium hydrideHCID 11076055Methyl 2-(2-(benzyloxy)phenyl)acetate

生成物 1

HCID 69942437Methyl 2-(2'-benzyloxyphenyl)-3-hydroxyacrylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
0 °C

実験手順

A mixture of methyl 2-benzyloxyphenylacetate (26.99 g) and methyl formate (126.62 g) in dry DMF (300 ml) was added dropwise to a stirred suspension of sodium hydride (50% disp. in oil, 10.13 g) in DMF (300 ml) at 0° C. After stirring at 0° C. for two hours the mixture was poured into water (1000 ml) and washed with ether (2×150 ml). The aqueous layer was acidified to pH4 with 6M hydrochloric acid then extracted with ether (2×350 ml). The extracts were dried and concentrated under reduced pressure to afford crude methyl 2-[2'-benzyloxyphenyl]-3-hydroxyacrylate as a yellow oil, infrared max. (film): 1720, 1660 cm-1.

後処理

  1. washwashed with ether (2×150 ml)
  2. extractionthen extracted with ether (2×350 ml)
  3. customThe extracts were dried
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-d1e60607c2834d78acefd19d08bf7e7c
出典データセット
uspto-grants-1991_10
特許番号
US05057146

反応ノート

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