Methyl formate → Methyl alpha-[2-(4-phenoxybut-1-yloxy)-phenyl]-beta-hydroxyacrylate

HRID 1085337

反応式

HRID 1085337 の反応式
[O:1]([CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][C:20]([O:22][CH3:23])=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:24](OC)=[O:25].[H-].[Na+]>C(OCC)C>[O:1]([CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19](=[CH:24][OH:25])[C:20]([O:22][CH3:23])=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 7865Methyl formateHCID 24758Sodium hydrideHCID 14550847Methyl 2-(4-phenoxybut-1-yloxy)-phenylacetate

生成物 1

HCID 67930312Methyl alpha-[2-(4-phenoxybut-1-yloxy)-phenyl]-beta-hydroxyacrylate収率 71%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

A mixture of 30 g (0.10 mole) of methyl 2-(4-phenoxybut-1-yloxy)-phenylacetate, 12.5 g (0.21 mole) of methyl formate and 100 ml of diethyl ether is added dropwise at room temperature to a suspension of 3.4 g (0.14 mole) of sodium hydride in 50 ml of diethyl ether. The mixture is stirred for 12 hours at room temperature and is then hydrolyzed by adding ice. The aqueous, alkaline phase is extracted with diethyl ether, acidified with dilute HCl and again extracted by shaking with diethyl ether. After the organic phase has been evaporated down, 21 g (71%) of methyl alpha-[2-(4-phenoxybut-1-yloxy)-phenyl]-β-hydroxyacrylate are obtained.

後処理

  1. additionby adding ice
  2. extractionThe aqueous, alkaline phase is extracted with diethyl ether
  3. extractionagain extracted
  4. stirringby shaking with diethyl ether
  5. customAfter the organic phase has been evaporated down

出典と根拠

ORDレコード
ord-1dd187cc3bf24b67b01ec4697ffcf142
出典データセット
uspto-grants-1991_04
特許番号
US05008438

関連ノート

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