3-(3-Methoxy-3-methylbut-1-yl)-5-methylcyclohexan-1-one → 3-(3-Methoxy-3-methylbutyl)-5-methylcyclohexanol

HRID 329478Notes

Reaction equation

HRID 329478 reaction equation
[CH3:1][O:2][C:3]([CH3:15])([CH3:14])[CH2:4][CH2:5][CH:6]1[CH2:11][CH:10]([CH3:12])[CH2:9][C:8](=[O:13])[CH2:7]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:1][O:2][C:3]([CH3:14])([CH3:15])[CH2:4][CH2:5][CH:6]1[CH2:11][CH:10]([CH3:12])[CH2:9][CH:8]([OH:13])[CH2:7]1

Participants

4

Reactant 2

HCID 147939943-(3-Methoxy-3-methylbut-1-yl)-5-methylcyclohexan-1-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 147939953-(3-Methoxy-3-methylbutyl)-5-methylcyclohexanolYield 77.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 3-(3-methoxy-3-methylbut-1-yl)-5-methylcyclohexan-1-one (0.50 g, 0.0024 mol) in tetrahydrofuran (1 mL) was added to a suspension of lithium aluminum hydride (0.10 g, 0.0027 mol) in tetrahydrofuran (1 mL) cooled to 0° C. The mixture was stirred at 20° C. for 16 h. Subsequent workup yielded 3-(3-methoxy-3-methylbutyl)-5-methylcyclohexanol (0.40 g) as a mixture of four diastereoisomers (ratio 2.8:15.3:79.2:2.8).

Sources & evidence

ORD record
ord-228d092e85604800b9352b9ed43206ae
Source dataset
uspto-grants-1990_01
Patent number
US04891447

Reaction notes

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