Aluminium lithium hydride → 4-({4-[Phenyl(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl}oxy)-1-butanol

HRID 2241051Notes

Reaction equation

HRID 2241051 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]1([C:13](=[C:29]2[CH2:34][C:33]([CH3:36])([CH3:35])[CH2:32][C:31]([CH3:38])([CH3:37])[CH2:30]2)[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][C:24](OCC)=[O:25])=[CH:16][CH:15]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C1COCC1>[C:7]1([C:13](=[C:29]2[CH2:34][C:33]([CH3:36])([CH3:35])[CH2:32][C:31]([CH3:38])([CH3:37])[CH2:30]2)[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][OH:25])=[CH:16][CH:15]=2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 68502642Ethyl 4-({4-[phenyl(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl}oxy)butanoate

Product 1

HCID 119926684-({4-[Phenyl(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl}oxy)-1-butanolYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The LAH reduction procedure described for 15 (example 5) was utilized using 36 (200 mg, 0.46 mmol), LAH (1 M solution in THF, 1.4 mL, 1.38 mmol) in THF (30 mL). The reaction was stirred for 0.5 h. Standard aqueous work-up followed by purification gave 126 mg (70%) of the title product 37 as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.28-7.24 (m, 2H), 7.18-7.14 (m, 3H), 7.07 (d, J=8.4 Hz, 2H), 6.79 (d, J=8.4 Hz, 2H), 3.97 (t, J=6.0 Hz, 2H), 3.71 (br m, 2H), 1.98 (s, 2H), 1.95 (s, 2H), 1.88-1.84 (pentet, J=6.0 Hz, 2H), 1.78-1.70 (pentet, J=5.6 Hz, 2H), 1.28 (s, 2H), 0.93 (s, 6H), 0.92 (s, 6H). LCMS (APCI): m/z 393 (M+H)+.

Workup

  1. customStandard aqueous work-up followed by purification

Sources & evidence

ORD record
ord-8d7d7815d0e8454582d88641cd7efd40
Source dataset
uspto-grants-2010_05
Patent number
US07723393B2

Reaction notes

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