Aluminium lithium hydride → HCID 67251171, compound

HRID 2426759Notes

Reaction equation

HRID 2426759 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][O:15][C:16]3[CH:25]=[CH:24][C:19]([C:20](OC)=[O:21])=[C:18]([F:26])[CH:17]=3)[CH:9]=2)=[C:4]([CH3:27])[CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][O:15][C:16]3[CH:25]=[CH:24][C:19]([CH2:20][OH:21])=[C:18]([F:26])[CH:17]=3)[CH:9]=2)=[C:4]([CH3:27])[CH:3]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57787703HCID 57787703, compound

Product 1

HCID 67251171HCID 67251171, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In an atmosphere of nitrogen, a THF solution of methyl 4-[(4′-chloro-2′-methylbiphenyl-3-yl)methoxy]-2-fluorobenzoate was dropwise added to a THF suspension of lithium aluminum hydride under cooling on an ice-methanol bath, followed by stirring at room temperature for 1 hour to obtain 4-[(4′-chloro-2′-methylbiphenyl-3-yl)methoxy]-2-fluorobenzyl alcohol. By adding manganese dioxide to a THF solution of the resulting 4-[(4′-chloro-2′-methylbiphenyl-3-yl)methoxy]-2-fluorobenzyl alcohol and stirring at 40° C. for 17 hours, 4-[(4′-chloro-2′-methylbiphenyl-3-yl)methoxy]-2-fluorobenzaldehyde was obtained.

Workup

  1. temperatureunder cooling on an ice-methanol bath

Sources & evidence

ORD record
ord-0062b78eba46421aa46c243211e84cc0
Source dataset
uspto-grants-2011_06
Patent number
US07968552B2

Reaction notes

Loading…