Ethanol → HCID 86740519、化合物

HRID 637322

反応式

HRID 637322 の反応式
[CH3:1][C:2]1([CH3:14])[CH:4]([CH:5]=O)[CH:3]1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[O:15]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(O)C.[Na]>O.C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:14])[C@H:4]([CH:5]=[C:22]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:23]([O:25][CH2:26][CH3:27])=[O:24])[C@H:3]1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]

参加物

7

反応物 4

HCID 702EthanolHCID 17365Acetic acid, 2-phenoxy-, ethyl esterHCID 5360545SodiumHCID 11735753Tert-butyl 3-formyl-2,2-dimethylcyclopropane-1-carboxylate

生成物 1

HCID 86740519HCID 86740519、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒2 回

反応条件

温度
20 °C

実験手順

9.9 g of tert.-butyl 2,2-dimethyl-3-formyl-cyclopropane-carboxylate and 28 g of ethyl phenoxyacetate were added dropwise at 0° C. to a mixture of 0.05 ml of ethanol, 1.25 g of sodium in small pieces and 25 ml of toluene and the solution was stirred at 20° C. for 16 hours. 20 ml of toluene were added thereto and the mixture was stirred for 4 hours and was poured into iced water. The mixture was extracted with methylene chloride and the organic phase was evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with a 7-3 hexane-ethyl acetate mixture to obtain 12.47 g of E or Z isomer of tert.-butyl (1R,trans) 2,2-dimethyl-3-[2-phenoxy-2-ethoxycarbonyl-ethenyl]-cyclopropane-carboxylate.

後処理

  1. stirringthe mixture was stirred for 4 hours
  2. extractionThe mixture was extracted with methylene chloride
  3. customthe organic phase was evaporated to dryness under reduced pressure
  4. customThe residue was chromatographed over silica gel
  5. washwas eluted with a 7-3 hexane-ethyl acetate mixture

出典と根拠

ORDレコード
ord-805ed1e8cbb24b90a570527abb9e86ae
出典データセット
uspto-grants-1985_12
特許番号
US04556666

関連ノート

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