Allyl bromide → HCID 53979547, compound

HRID 637383Notes

Reaction equation

HRID 637383 reaction equation
[CH:1]1([C:6]([CH2:21][CH3:22])=[C:7]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH2:25](Br)[CH:26]=[CH2:27]>COCCOC>[CH:1]1([C:6]([CH2:21][CH3:22])=[C:7]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:27][CH:26]=[CH2:25])=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 53646607HCID 53646607, compound

Product 1

HCID 53979547HCID 53979547, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

2.92 g (10 mmol) of pure E- or Z-isomer of 2-cyclopentyl-1-(p-hydroxyphenyl)-1-phenyl-1-butene in dry DME was added under nitrogen atmosphere to a stirred suspension of sodium hydride in DME (0.6 g of 50-60% dispersion from which the oil had been removed by washing with dry DME). After stirring for 30 minutes at room temperature, 1.44 g (12 mmol) of allyl bromide was added. The mixture was refluxed for 3 hours. Ice water was added. The water layer was extracted with ether and the combined organic layers washed with diluted sodium hydroxide and water and dried. After evaporation of the solvent the residue was 3.1 g. In the case of the E-isomer the semisolid product was purified by chromatography over silica gel using methylene chloride as eluent. The Z-isomer was purified by recrystallization from methanol, mp. 82°-84° C.

Workup

  1. customhad been removed
  2. washby washing with dry DME)
  3. temperatureThe mixture was refluxed for 3 hours
  4. extractionThe water layer was extracted with ether
  5. washthe combined organic layers washed with diluted sodium hydroxide and water
  6. customdried
  7. customAfter evaporation of the solvent the residue
  8. customIn the case of the E-isomer the semisolid product was purified by chromatography over silica gel
  9. customThe Z-isomer was purified by recrystallization from methanol, mp. 82°-84° C.

Sources & evidence

ORD record
ord-66a98c0a60414995ad7584a99a5dd98e
Source dataset
uspto-grants-1985_12
Patent number
US04556677

Reaction notes

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