Hydrogen Peroxide → 3-(1-{[Tert-butyl(dimethyl)silyl]oxy}cyclohexyl)propan-1-ol

HRID 44722Notes

Reaction equation

HRID 44722 reaction equation
B.[CH2:2]([C:5]1([O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)[CH:3]=[CH2:4].[OH-:19].[Na+].OO>O1CCCC1.C(OCC)C.O>[Si:12]([O:11][C:5]1([CH2:2][CH2:3][CH2:4][OH:19])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:13])[CH3:14]

Participants

8

Reactant 4

HCID 784Hydrogen PeroxideHCID 6331BoraneHCID 14798Sodium HydroxideHCID 57457814[(1-Allylcyclohexyl)oxy](tert-butyl)dimethylsilane

Product 1

HCID 574578153-(1-{[Tert-butyl(dimethyl)silyl]oxy}cyclohexyl)propan-1-olYield 79%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of borane in tetrahydrofuran (1 M, 15.7 mL, 15.7 mmol) was added to a solution of [(1-allylcyclohexyl)oxy](tert-butyl)dimethylsilane (8.00 g, 31.4 mmol) in tetrahydrofuran. After 2 h, water (5 mL) was added dropwise, followed by 3 M NaOH (6 mL), followed by dropwise addition of 30% aqueous hydrogen peroxide (6 mL). The mixture was stirred at rt for 1 h, then was diluted with diethyl ether (100 mL) and water (70 mL). The layers were separated and the aqueous layer was extracted with diethyl ether (2×35 mL). The combined organic layers were washed with brine (90 mL), dried over MgSO4, filtered, and concentrated to yield a colorless oil that was purified using HPFC (silica gel, gradient elution with 2-30% ethyl acetate/hexanes) to afford pure 3-(1-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)propan-1-ol (6.80 g, 79%).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with diethyl ether (2×35 mL)
  3. washThe combined organic layers were washed with brine (90 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield a colorless oil that
  8. customwas purified
  9. washHPFC (silica gel, gradient elution with 2-30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-9222fa0966a749208fd54afd711cac12
Source dataset
uspto-grants-2013_09
Patent number
US08541438B2

Reaction notes

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