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

HRID 1181649노트

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HRID 1181649 반응식
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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

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온도
27 °C

실험 절차

To a solution of 1-(3,5-dimethoxyphenyl)-1-(hex-1-enyl)-cyclopentane (1 equiv.) in dry hexane (0.05 M) 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.

후처리

  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

출처 및 근거

ORD 기록
ord-c8d0642d63924852821d1937da3e3645
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07285683B2

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