Aluminium lithium hydride → [4'-(3-Fluoro-3-methylbutoxy)-2,2'-dimethylbiphenyl-3-yl]methanol

HRID 2426774Notes

Reaction equation

HRID 2426774 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]([CH3:31])([CH3:30])[CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24](OC)=[O:25])[C:19]=2[CH3:28])=[C:14]([CH3:29])[CH:13]=1>C1COCC1>[F:7][C:8]([CH3:31])([CH3:30])[CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][OH:25])[C:19]=2[CH3:28])=[C:14]([CH3:29])[CH:13]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67250088Methyl 4'-(3-fluoro-3-methylbutoxy)-2,2'-dimethylbiphenyl-3-carboxylate

Product 1

HCID 57787394[4'-(3-Fluoro-3-methylbutoxy)-2,2'-dimethylbiphenyl-3-yl]methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In an atmosphere of nitrogen, a mixture of 1-bromo-4-(3-fluoro-3-methylbutoxy)-2-methylbenzene, methyl 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate, palladium acetate, dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine, tripotassium phosphate, toluene and water was stirred at 80° C. for 12 hours to obtain methyl 4′-(3-fluoro-3-methylbutoxy)-2,2′-dimethylbiphenyl-3-carboxylate. Lithium aluminum hydride was added to a THF solution of the resulting methyl 4′-(3-fluoro-3-methylbutoxy)-2,2′-dimethylbiphenyl-3-carboxylate under ice-cooling, followed by warming up to room temperature and stirring for 1 hour to obtain [4′-(3-fluoro-3-methylbutoxy)-2,2′-dimethylbiphenyl-3-yl]methanol.

Workup

  1. temperaturecooling

Sources & evidence

ORD record
ord-f1100908d03d45e6a87119e31bf968c5
Source dataset
uspto-grants-2011_06
Patent number
US07968552B2

Reaction notes

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