Potassium Carbonate → HCID 86760619、化合物

HRID 2057331ノート

反応式

HRID 2057331 の反応式
[CH2:1]([O:8][C:9](=[O:20])[N:10]([C@H:12]1[CH2:17][CH2:16][C@H:15]([CH:18]=O)[CH2:14][CH2:13]1)[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br-].[Br:22][CH2:23][CH2:24][CH2:25][CH2:26][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>CC(O)(CC)C>[CH2:1]([O:8][C:9](=[O:20])[N:10]([CH:12]1[CH2:17][CH2:16][CH:15]([CH:18]=[CH:26][CH2:25][CH2:24][CH2:23][Br:22])[CH2:14][CH2:13]1)[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 2733851(4-Bromobutyl)triphenylphosphanium bromideHCID 178485996HCID 178485996、化合物

生成物 1

HCID 86760619HCID 86760619、化合物

試薬・触媒・溶媒 1

HCID 64052-Methyl-2-butanol溶媒

実験手順

A solution of 126.5 g (459.4 mmol) of trans-(4-Formyl-cyclohexyl)-methyl-carbamic acid benzyl ester in 1.27 l 2-methyl-2-butanol was treated with 263.6 g (551.3 mmol) (4-bromobutyl)triphenylphosphonium bromide and 254 g (1838 mmol) of K2CO3 and was heated at reflux for 3.5 h. The reaction was cooled (RT), filtered and evaporated. The residue was suspended in hexane (1.8 l, first at RT then at 0° C.) and filtered. Purification by column chromatography on silica gel (hexane/EtOAc 4:1) gave 149.9 g (83%) of trans-(1 E/Z)-[4-(5-Bromo-pent-1-enyl)-cyclohexyl]-methyl-carbamic acid benzyl ester, MS: 293 (M, 1Br).

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 3.5 h
  3. filtrationfiltered
  4. customevaporated
  5. filtrationfirst at RT then at 0° C.) and filtered
  6. customPurification by column chromatography on silica gel (hexane/EtOAc 4:1)

出典と根拠

ORDレコード
ord-4005ec2e19c74c5c82a97a7853be0a42
出典データセット
uspto-grants-2008_02
特許番号
US07335687B2

反応ノート

読み込み中…