Lithium tri-s-butylborohydride → 3-(3-Methoxy-3-methylbut-1-yl)-5,5-dimethylcyclohexan-1-ol

HRID 1088013Notes

Reaction equation

HRID 1088013 reaction equation
C([BH-](C(CC)C)C(CC)C)(CC)C.[Li+].[CH3:15][O:16][C:17]([CH3:30])([CH3:29])[CH2:18][CH2:19][CH:20]1[CH2:25][C:24]([CH3:27])([CH3:26])[CH2:23][C:22](=[O:28])[CH2:21]1>O1CCCC1>[CH3:15][O:16][C:17]([CH3:30])([CH3:29])[CH2:18][CH2:19][CH:20]1[CH2:25][C:24]([CH3:26])([CH3:27])[CH2:23][CH:22]([OH:28])[CH2:21]1

Participants

4

Reactant 2

HCID 3611392Lithium tri-s-butylborohydrideHCID 147939963-(3-Methoxy-3-methylbutyl)-5,5-dimethylcyclohexan-1-one

Product 1

HCID 147939973-(3-Methoxy-3-methylbut-1-yl)-5,5-dimethylcyclohexan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To lithium tri-sec-butylborohydride (2.7 mL of a 1.0 M solution in tetrahydrofuran, 0.0027 mol) cooled to -65~C was added 3-(3-methoxy-3-methylbutyl)-5,5-dimethylcyclohexan-1-one (0.5 g, 0.0022 mol) dissolved in tetrahydrofuran (3.5 mL). The mixture was allowed to stir at 25~C for 16 hours. Workup yielded 3-(3-methoxy-3-methylbut-1-yl)-5,5-dimethylcyclohexan-1-ol, bp1.0 210-21218 C (0.31 g). This compound was determined to possess a warm woody note. NMR(CDC13)δ0.9(s,3H), 1.1 (s,3H), 1.2(s,6H), 1.2-1.4(m,4H), 1.4-1.7(m,6H), 1.7-1.9(m,2H), 3.2(s,3H), 4.2(m, 1H); IR(neat) 3425, 2970, 2940, 1470, 1365, 1080 cm-1 ; MS(m/e) 43, 55, 73, 125, 163, 213, 214.

Sources & evidence

ORD record
ord-c8d9ce84ec414b9eabe8e5523d61591c
Source dataset
uspto-grants-1990_10
Patent number
US04960946

Reaction notes

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