Aluminium lithium hydride → [4-(4-Benzyloxy-phenyl)-1-methyl-cyclohex-3-enyl]-methanol

HRID 351431Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH2:20][CH2:19][C:18]([CH3:23])([CH:21]=[O:22])[CH2:17][CH:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH2:20][CH2:19][C:18]([CH2:21][OH:22])([CH3:23])[CH2:17][CH:16]=2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a cooled solution of 4-(4-benzyloxy-phenyl)-1-methyl-cyclohex-3-ene carbaldehyde (0.41 g, 1.33 mmol) in THF (10.0 mL) was added to LAH (0.100 g, 2.70 mmol) and the reaction mixture stirred at 0° C. for 3 h. The reaction mixture was then quenched by methanol followed by aqueous HCl (1N, 2 mL) until all of the black/brown precipitate was dissolved. The resulting mixture was extracted with ethyl acetate (2×30 mL). The combined organic layers were washed with brine, dried over MgSO4 and purified by SiO2 (50% ethyl acetate/hexane) to yield [4-(4-benzyloxy-phenyl)-1-methyl-cyclohex-3-enyl]-methanol as a liquid.

Workup

customThe reaction mixture was then quenched by methanol
dissolutionwas dissolved
extractionThe resulting mixture was extracted with ethyl acetate (2×30 mL)
washThe combined organic layers were washed with brine
dry with materialdried over MgSO4
custompurified by SiO2 (50% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-08dbc96139a943e7a2e01d1362c8e38c
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07183445B2

Reaction notes

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