Tetrabutylammonium Fluoride → Ethyl 6-(3,5-difluoro-4-hydroxybenzyl)-8-[5-fluoro-2-(4'-trifluoromethylbiphenyl-4-ylmethoxy)-phenyl]oct-7-enoate

HRID 1921882Notes

Reaction equation

HRID 1921882 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:43]=[C:44]([F:57])[C:45]=1[O:46][Si](C(C)C)(C(C)C)C(C)C)[CH2:5][CH:6]([CH:16]=[CH:17][C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1[O:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][CH:34]=2)=[CH:29][CH:28]=1)[CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:43]=[C:44]([F:57])[C:45]=1[OH:46])[CH2:5][CH:6]([CH:16]=[CH:17][C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1[O:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:34]=[CH:35][C:36]([C:39]([F:41])([F:42])[F:40])=[CH:37][CH:38]=2)=[CH:29][CH:28]=1)[CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 76678040Ethyl 6-(3,5-difluoro-4-triisopropylsilanyloxybenzyl)-8-[5-fluoro-2-(4'-trifluoromethylbiphenyl-4-ylmethoxy)phenyl]oct-7-enoate

Product 1

HCID 76678032Ethyl 6-(3,5-difluoro-4-hydroxybenzyl)-8-[5-fluoro-2-(4'-trifluoromethylbiphenyl-4-ylmethoxy)-phenyl]oct-7-enoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

720 mg (0.89 mmol) of ethyl 6-(3,5-difluoro-4-triisopropylsilanyloxybenzyl)-8-[5-fluoro-2-(4′-trifluoromethylbiphenyl-4-ylmethoxy)phenyl]oct-7-enoate are introduced into 15 ml of THF at 0° C. under argon, 1.77 ml (1.77 mmol) of a 1 M solution of tetra-n-butylammonium fluoride in THF are added, and the mixture is stirred at room temperature until reaction is complete. All the volatile components are removed in vacuo. The resulting crude product is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 7:1). 400 mg (68% of theory) of the title compound are obtained as an E/Z mixture (2:1).

Workup

  1. customAll the volatile components are removed in vacuo
  2. customThe resulting crude product is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 7:1)

Sources & evidence

ORD record
ord-1c1baf2a746543afa47a32928f0265a2
Source dataset
uspto-grants-2012_05
Patent number
US08173704B2

Reaction notes

Loading…