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

HRID 269432Notes

Reaction equation

HRID 269432 reaction equation
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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
27 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-368d06d5b9a14d78a9320701739f0687
Source dataset
uspto-grants-2008_11
Patent number
US07446229B2

Reaction notes

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