Pyridine → (S)alpha-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-[(Z) 3-(2,2,2trifluoroethoxy)-3-oxo-1-propenyl]-cyclopropane-carboxylate

HRID 1719733ノート

反応式

HRID 1719733 の反応式
[CH3:1][C:2]1([CH3:18])[C@@H:4](/[CH:5]=[CH:6]\[C:7](=[O:14])[O:8][CH2:9][C:10]([F:13])([F:12])[F:11])[C@H:3]1[C:15]([OH:17])=[O:16].N1C=CC=CC=1.C1(N=C=NC2CCCCC2)CCCCC1.O[C@@H:41]([C:44]1[CH:49]=[CH:48][CH:47]=[C:46]([O:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH:45]=1)[C:42]#[N:43]>C(Cl)Cl>[CH3:1][C:2]1([CH3:18])[C@@H:4](/[CH:5]=[CH:6]\[C:7]([O:8][CH2:9][C:10]([F:13])([F:11])[F:12])=[O:14])[C@H:3]1[C:15]([O:17][C@H:41]([C:42]#[N:43])[C:44]1[CH:49]=[CH:48][CH:47]=[C:46]([O:50][C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=2)[CH:45]=1)=[O:16]

参加物

6

反応物 4

HCID 1049PyridineHCID 10868DicyclohexylcarbodiimideHCID 9837437(2S)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrileHCID 13390085(1R,cis)2,2-dimethyl-3-[(Z)3-oxo-3-(2,2,2-trifluoroethoxy)-1-propenyl]-cyclopropane-carboxylic acid

生成物 1

HCID 13188366(S)alpha-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-[(Z) 3-(2,2,2trifluoroethoxy)-3-oxo-1-propenyl]-cyclopropane-carboxylate収率 57.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

1.3 g of (1R,cis) 2,2-dimethyl-3-[(Z) 3-oxo-3 (2,2,2-trifluoroethoxy)-1-propenyl]-cyclopropane-carboxylic acid, 0.1 ml of pyridine and 15 ml of methylene chloride were mixed with agitation and then 1.05 g of dicyclohexylcarbodiimide were added thereto. A solution of 1.35 g of (S)α-hydroxy-3-phenoxy-benzene-acetonitrile in 5 ml of methylene chloride were then added to the mixture which was stirred for 5 hours at ambient temperature and then was filtered. The filter was rinsed with methylene chloride and 2N hydrochloric acid was added to the filtrate. The decanted organic phase was washed with water, dried and evaporated to dryness. The oil residue was chromatographed over silica gel and was eluted with 95-5 cyclohexane ethyl acetate mixture to obtain 1.33 g of (S)α-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-[(Z) 3-(2,2,2-trifluoroethoxy)-3-oxo-1-propenyl]-cyclopropane-carboxylate with a specific rotation of [α]D20 =+42°±2° (c= 0.7% in benzene).

後処理

  1. filtrationwas filtered
  2. washThe filter was rinsed with methylene chloride and 2N hydrochloric acid
  3. additionwas added to the filtrate
  4. washThe decanted organic phase was washed with water
  5. customdried
  6. customevaporated to dryness
  7. customThe oil residue was chromatographed over silica gel
  8. washwas eluted with 95-5 cyclohexane ethyl acetate mixture

出典と根拠

ORDレコード
ord-973272ba63184ca285034cc130b700cf
出典データセット
uspto-grants-1985_09
特許番号
US04542142

反応ノート

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