Triethylamine → 4-Fluoro-3-phenoxybenzyl 4-(4-fluorophenyl)-2-isopropyl-3-butenoate

HRID 903834Notes

Reaction equation

HRID 903834 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C.[F:24][C:25]1[CH:30]=[CH:29][C:28]([CH:31]=[CH:32][CH:33]([CH:37]([CH3:39])[CH3:38])[C:34](O)=[O:35])=[CH:27][CH:26]=1>CCOCC>[F:24][C:25]1[CH:26]=[CH:27][C:28]([CH:31]=[CH:32][CH:33]([CH:37]([CH3:39])[CH3:38])[C:34]([O:7][CH2:6][C:5]2[CH:8]=[CH:9][C:2]([F:1])=[C:3]([O:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:4]=2)=[O:35])=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12874224(4-Fluoro-3-phenoxyphenyl)methanolHCID 538855142-Isopropyl-4-(4-fluorophenyl)-3-butenoic acid

Product 1

HCID 542271534-Fluoro-3-phenoxybenzyl 4-(4-fluorophenyl)-2-isopropyl-3-butenoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred solution of 4-fluoro-3-phenoxybenzyl alcohol (0.22 g, 0.99 mmol) and triethylamine (0.14 g, 1.38 mmol) in ether (about 15 ml), under nitrogen, is added by syringe a solution of the acid chloride of 4-(4-fluorophenyl)-2-isopropyl-3-butenoic acid (1.5 mmol) in ether. The mixture is stirred for 30 minutes and then quenched with saturated aqueous sodium bicarbonate. The ether phase is washed with aqueous sodium bicarbonate, water and brine and filtered through silica. Evaporation of solvent, followed by thin layer chromatography using a circular chromatograph, eluting with 20 percent ether/hexane, gives 4-fluoro-3-phenoxybenzyl 4-(4-fluorophenyl)-2-isopropyl-3-butenoate.

Workup

  1. customquenched with saturated aqueous sodium bicarbonate
  2. washThe ether phase is washed with aqueous sodium bicarbonate, water and brine
  3. filtrationfiltered through silica
  4. customEvaporation of solvent
  5. washeluting with 20 percent ether/hexane

Sources & evidence

ORD record
ord-575f23f21e424253b649cf25e5e672f4
Source dataset
uspto-grants-1980_10
Patent number
US04229368

Reaction notes

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