Sodium hydride → Cyclopentanol, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-

HRID 750995Notes

Reaction equation

HRID 750995 reaction equation
[H-].[Na+].[CH:3]1([OH:9])[CH2:7][CH2:6][CH:5]([OH:8])[CH2:4]1.[Si:10](Cl)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]>C1COCC1.C(OC(=O)C)C>[Si:10]([O:8][CH:5]1[CH2:6][CH2:7][CH:3]([OH:9])[CH2:4]1)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chlorideHCID 100165Cyclopentane-1,3-diol

Product 1

HCID 21938628Cyclopentanol, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-Yield 35%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium Hydride (3.77 g, 0.094 mol, 60% in mineral oil) was added to a solution of 1,3-cyclopentanediol (9.62 g, 0.094 mol) in 100 mL of THF. A slight generation of gas was observed. After stirring at room temperature for 1 h, tert-butyldimethylsilyl chloride (14.2 g, 0.094 mol) was added and the mixture was stirred at room temperature over night. The reaction mixture was diluted with 500 mL of ethylacetate and washed with 125 mL of 10% K2CO3, brine, and dried over Na2SO4. The solution was concentrated and dried in vacuo to give 20.3 g of crude product as a colorless oil. Further purification over SiO2 using a gradient elution 5% EtOAc/hexanes to 10% EtOAc/hexanes provided the desired compound as a colorless oil (7.1 g, 35% yield).

Workup

  1. stirringthe mixture was stirred at room temperature over night
  2. washwashed with 125 mL of 10% K2CO3, brine
  3. dry with materialdried over Na2SO4
  4. concentrationThe solution was concentrated
  5. customdried in vacuo
  6. customto give 20.3 g of crude product as a colorless oil
  7. customFurther purification over SiO2 using
  8. washa gradient elution 5% EtOAc/hexanes to 10% EtOAc/hexanes

Sources & evidence

ORD record
ord-bf27d1059eac49128dc1dcf22b67f0d6
Source dataset
uspto-grants-2008_07
Patent number
US07405230B2

Reaction notes

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