Dichloromethane → (S)alpha-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-(2,2,2-trichloroethoxycarbonylethynyl)-cyclopropane-carboxylate

HRID 464452

反応式

HRID 464452 の反応式
C1(N=C=NC2CCCCC2)CCCCC1.[CH3:16][C:17]1([CH3:33])[C@@H:19]([C:20]#[C:21][C:22]([O:24][CH2:25][C:26]([Cl:29])([Cl:28])[Cl:27])=[O:23])[C@H:18]1[C:30]([OH:32])=[O:31].C(Cl)Cl.[C:37]([C@@H:39](O)[C:40]1[CH:45]=[CH:44][CH:43]=[C:42]([O:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[CH:41]=1)#[N:38]>N1C=CC=CC=1>[CH3:16][C:17]1([CH3:33])[C@@H:19]([C:20]#[C:21][C:22]([O:24][CH2:25][C:26]([Cl:28])([Cl:29])[Cl:27])=[O:23])[C@H:18]1[C:30]([O:32][C@H:39]([C:37]#[N:38])[C:40]1[CH:45]=[CH:44][CH:43]=[C:42]([O:46][C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=2)[CH:41]=1)=[O:31]

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 10868DicyclohexylcarbodiimideHCID 9837437(2S)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrileHCID 13093792(1R,cis)2,2-dimethyl-3-(2,2,2-trichloroethoxycarbonylethynyl)-cyclopropane-carboxylic acid

生成物 1

HCID 13093794(S)alpha-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-(2,2,2-trichloroethoxycarbonylethynyl)-cyclopropane-carboxylate収率 76.3%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

6.2 g of dicyclohexylcarbodiimide were added to a mixture of 9.5 g of the product of Step B, 30 ml of methylene chloride and 3 ml of pyridine and after stirring for 30 minutes, 6.8 g of (S)α-cyano-3-phenoxy-benzyl alcohol were added to the mixture. The mixture was stirred for 90 minutes and was filtered and the filtrate was washed with N hydrochloric acid and then with water until the wash water was neutral, dried and evaporated to dryness. The 16.3 g of oil residue were chromatographed over silica gel and eluted with a 97-3 benzene-ethyl acetate mixture to obtain 12 g of (S)α-cyano-3-phenoxy-benzyl(1R,cis)2,2-dimethyl-3-(2,2,2-trichloroethoxycarbonyl-ethynyl]-cyclopropane-carboxylate melting at 101° C.

後処理

  1. stirringThe mixture was stirred for 90 minutes
  2. filtrationwas filtered
  3. washthe filtrate was washed with N hydrochloric acid
  4. customdried
  5. customevaporated to dryness
  6. customThe 16.3 g of oil residue were chromatographed over silica gel
  7. washeluted with a 97-3 benzene-ethyl acetate mixture

出典と根拠

ORDレコード
ord-fb8f31e3810f46fe9769b7b05cfef2eb
出典データセット
uspto-grants-1985_10
特許番号
US04547522

関連ノート

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