Water → Cyclohexanemethanol, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, cis-

HRID 1873563Notes

Reaction equation

HRID 1873563 reaction equation
[Si:1]([O:8][CH:9]1[CH2:14][CH2:13][CH:12]([C:15](OC)=[O:16])[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[K+]>C(OCC)C>[Si:1]([O:8][CH:9]1[CH2:10][CH2:11][CH:12]([CH2:15][OH:16])[CH2:13][CH2:14]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22167752Methyl trans-4-[(tert-butyldimethylsilyl)oxy]cyclohexanecarboxylate

Product 1

HCID 57999111Cyclohexanemethanol, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, cis-

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

200 mg (0.59 mmol) of the crude product from Example 9A (80% pure) are dissolved in 1.5 ml of diethyl ether. At RT, this solution is added dropwise to a suspension of 13.4 mg (0.35 mmol) of lithium aluminum hydride in 1.5 ml of diethyl ether. The mixture is stirred at RT for 20 h. 12 μl of water, 12 μl of 15% strength aqueous potassium hydroxide solution and 3 ml of diethyl ether are then added, and the mixture is stirred at RT for 30 min. The reaction mixture is then filtered through a cartridge charged with 2.4 g of silica gel and 2.4 g of Extrelut (mobile phase: dichloromethane/ethanol 10:1). The solvent is removed on a rotary evaporator and the residue is purified chromatographically on silica gel 60 (mobile phase: gradient cyclohexane/ethyl acetate 20:1→10:1).

Workup

  1. stirringthe mixture is stirred at RT for 30 min
  2. filtrationThe reaction mixture is then filtered through a cartridge
  3. additioncharged with 2.4 g of silica gel and 2.4 g of Extrelut (mobile phase: dichloromethane/ethanol 10:1)
  4. customThe solvent is removed on a rotary evaporator
  5. customthe residue is purified chromatographically on silica gel 60 (mobile phase: gradient cyclohexane/ethyl acetate 20:1→10:1)

Sources & evidence

ORD record
ord-e42bc4d2a7e04d0782c52a155831e339
Source dataset
uspto-grants-2012_11
Patent number
US08304412B2

Reaction notes

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