Sodium hydride → HCID 22097916、化合物

HRID 1154401ノート

反応式

HRID 1154401 の反応式
C(OP([CH:9]([F:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])(OCC)=O)C.[CH3:16][C:17]1([CH3:25])[CH:19]([CH:20]=O)[CH:18]1[C:22]([OH:24])=[O:23].[H-].[Na+].P(O)(O)([O-])=O.[Na+]>COCCOC>[CH3:16][C:17]1([CH3:25])[CH:19](/[CH:20]=[C:9](/[F:15])\[C:10](=[O:11])[O:12][CH2:13][CH3:14])[CH:18]1[C:22]([OH:24])=[O:23]

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 1794493-Formyl-2,2-dimethylcyclopropane-1-carboxylic acidHCID 2734865Triethyl 2-fluoro-2-phosphonoacetateHCID 23672064Monosodium phosphate

生成物 1

HCID 22097916HCID 22097916、化合物

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒2 回

反応条件

温度
5 °C

実験手順

A solution of 7.7 g of ethyl diethyl-phosphono-fluoro-acetate (prepared by process of Ann. Chem., 1964, p. 674), 60 ml of 1,2-dimethoxyethane and 4 g of (1R, trans) 2,2-dimethyl-3-formyl-cyclopropane-carboxylic acid was added over 30 minutes at 2° to 10° C. to a suspension of 2.6 g of a 60% sodium hydride in oil suspension and 60 ml of 1,2-dimethoxyethane and the mixture was stirred at 5° C. for 15 minutes, and then at room temperature for 3 hours. The resulting solution was poured into aqueous monosodium phosphate solution at 5° C. and the mixture was stirred for 10 minutes. The mixture was extracted with ethyl acetate and the organic phase was washed with water, dried and evaporated to dryness at 40° C. under reduced pressure to obtain 6.5 g of an oil residue. The latter was chromatographed over silica gel and was eluted with a 70-30-1 hexane-ethyl acetate-acetic acid mixture to obtain 4 g of (1R,trans) 2,2-dimethyl-3(E)-[2-fluoro-3-oxo-3-ethoxypropenyl]-cyclopropane-1-carboxylic acid

後処理

  1. waitat room temperature for 3 hours
  2. stirringthe mixture was stirred for 10 minutes
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe organic phase was washed with water
  5. customdried
  6. customevaporated to dryness at 40° C. under reduced pressure

出典と根拠

ORDレコード
ord-22688ebad8834bf2ad3091219131042f
出典データセット
uspto-grants-1984_12
特許番号
US04489093

反応ノート

読み込み中…