Propyltriphenylphosphonium bromide → 1-Carbobenzoxy-4-(1-butylidene)piperidine

HRID 223369

反応式

HRID 223369 の反応式
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)CC.[C:29]([N:39]1[CH2:44][CH2:43][C:42](=O)[CH2:41][CH2:40]1)([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30]>O1CCCC1>[C:29]([N:39]1[CH2:44][CH2:43][C:42](=[CH:1][CH2:2][CH2:3][CH3:4])[CH2:41][CH2:40]1)([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30]

参加物

5

反応物 3

HCID 80374Propyltriphenylphosphonium bromideHCID 643496Benzyl 4-oxopiperidine-1-carboxylateHCID 178418339Butyllithium

生成物 1

HCID 205220201-Carbobenzoxy-4-(1-butylidene)piperidine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Butyl lithium (44 ml of 1.6 M in hexane) was added slowly to a stirred suspension of 27 g of (n-propyl)triphenylphosphonium bromide in 350 ml of tetrahydrofuran and the resulting solution was refluxed for 1 hour. The mixture was cooled in an ice bath and 18 g of N-carbobenzyloxy-4-piperidone was added. After stirring at room temperature of 0.5 hour, the solution was refluxed for 2 hours. The cooled mixture was concentrated under reduced pressure, partitioned between ether and water, and the ether layer was dried (sodium sulfate) and evaporated. The residue was filtered through silica gel with 20% ethyl acetate-hexane to give 10 g of 1-carbobenzoxy-4-(1-butylidene)piperidine as a colorless oil.

後処理

  1. temperaturethe resulting solution was refluxed for 1 hour
  2. temperatureThe mixture was cooled in an ice bath
  3. temperaturethe solution was refluxed for 2 hours
  4. concentrationThe cooled mixture was concentrated under reduced pressure
  5. custompartitioned between ether and water
  6. dry with materialthe ether layer was dried (sodium sulfate)
  7. customevaporated
  8. filtrationThe residue was filtered through silica gel with 20% ethyl acetate-hexane

出典と根拠

ORDレコード
ord-f068b0d416624defa98b220467acb3f2
出典データセット
uspto-grants-1982_10
特許番号
US04353901

関連ノート

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