Ethanolamine → 5-[1-(Hex-1-enyl)-cyclopentyl]resorcinol

HRID 269432ノート

反応式

HRID 269432 の反応式
C[O:2][C:3]1[CH:4]=[C:5]([C:11]2([CH:16]=[CH:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:6]=[C:7]([O:9]C)[CH:8]=1.C(CN)O>CCCCCC.C1COCC1>[CH:16]([C:11]1([C:5]2[CH:4]=[C:3]([OH:2])[CH:8]=[C:7]([CH:6]=2)[OH:9])[CH2:15][CH2:14][CH2:13][CH2:12]1)=[CH:17][CH2:18][CH2:19][CH2:20][CH3:21]

参加物

5

反応物 2

HCID 700EthanolamineHCID 692046641-(3,5-Dimethoxyphenyl)-1-(hex-1-enyl)-cyclopentane

生成物 1

HCID 692058965-[1-(Hex-1-enyl)-cyclopentyl]resorcinol収率 82%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

反応条件

温度
27 °C

実験手順

To a solution of 1-(3,5-dimethoxyphenyl)-1-(hex-1-enyl)-cyclopentane (1 equiv.) in dry hexane (0.05M) at 0° C. under an argon atmosphere was added 9-iodo-9-BBN (2.3 equiv., 1M solution in hexane). The mixture was stirred at the same temperature for 3.5 h and then the reaction temperature was raised to 27° C. Stirring was continued at that temperature until completion of the reaction. The volatiles were removed in vacuo, the residual oil was dissolved in diethyl ether, and a solution of ethanolamine (2.4 equiv.) in THF (1.4 M) was added causing spontaneous precipitation of the 9-BBN.ethanolamine adduct. The suspension was stirred for 2.5 h, the white precipitate was filtered off and the filtrate was evaporated under reduced pressure to give an oil. Purification by flash column chromatography on silica gel using 40% diethyl ether—petroleum ether as eluent afforded the title compound in 82% yield.

後処理

  1. stirringStirring
  2. customwas continued at that temperature until completion of the reaction
  3. customThe volatiles were removed in vacuo
  4. dissolutionthe residual oil was dissolved in diethyl ether
  5. customprecipitation of the 9-BBN
  6. stirringThe suspension was stirred for 2.5 h
  7. filtrationthe white precipitate was filtered off
  8. customthe filtrate was evaporated under reduced pressure
  9. customto give an oil
  10. customPurification by flash column chromatography on silica gel using 40% diethyl ether—petroleum ether as eluent

出典と根拠

ORDレコード
ord-368d06d5b9a14d78a9320701739f0687
出典データセット
uspto-grants-2008_11
特許番号
US07446229B2

反応ノート

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