Lithium tri-s-butylborohydride → 3-(3-Methoxy-3-methylbutyl)-5-methylcyclohexanol

HRID 483697Notes

Reaction equation

HRID 483697 reaction equation
C([BH-](C(CC)C)C(CC)C)(CC)C.[Li+].[CH3:15][O:16][C:17]([CH3:29])([CH3:28])[CH2:18][CH2:19][CH:20]1[CH2:25][CH:24]([CH3:26])[CH2:23][C:22](=[O:27])[CH2:21]1>O1CCCC1>[CH3:15][O:16][C:17]([CH3:28])([CH3:29])[CH2:18][CH2:19][CH:20]1[CH2:25][CH:24]([CH3:26])[CH2:23][CH:22]([OH:27])[CH2:21]1

Participants

4

Reactant 2

HCID 3611392Lithium tri-s-butylborohydrideHCID 147939943-(3-Methoxy-3-methylbut-1-yl)-5-methylcyclohexan-1-one

Product 1

HCID 147939953-(3-Methoxy-3-methylbutyl)-5-methylcyclohexanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of lithium tri-sec-butylborohydride (267 mL of a 1M solution in tetrahydrofuran, 0.27 mol) was added to a cooled (-65~C.) solution of 3-(3-methoxy-3-methylbutyl)-5 methylcyclohexan-1-one (48.6 g, 0.22 mol) dissolved in tetrahydrofuran (350 mL). The solution was stirred at 25~C. for 16 hours and was quenched by addition of sodium hydroxide (10% aqueous, 165 mL) followed by hydrogen peroxide (30% aqueous, 170 mL). Workup yielded 3-(3-methoxy-3-methylbutyl)-5-methyl cyclohexan-1-ol as a mixture of diastereoisomers (ratio 90.1:7.2:2.7), bp0.75 120-122~C. (40.7 g). This compound and mixtures of diastereomers possess strong, tenacious, sandalwoody, musky notes. NMR(CDCl3) δ 0.6 (q,1H), 0.9(d,3H), 1.0-1.1(m,2H), 1.1(s,6H), 1.2-1.3 (m,2H), 1.4-1.6(m,2H), 1.6-1.9(m,5H), 2.2(brs,1H), 3.2(s,3H), 4.1(m,1H). IR(neat) 2400, 2975, 2925, 1460, 1385, 1365, 1210, 1090, 1015 cm-1 ; MS(m/e) 43, 73, 93, 111, 149, 167, 182, 199, 200.

Workup

  1. customwas quenched by addition of sodium hydroxide (10% aqueous, 165 mL)

Sources & evidence

ORD record
ord-0b95f658b12c44d78aa6524d8e706d72
Source dataset
uspto-grants-1993_07
Patent number
US05225608

Reaction notes

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