Sodium hydride → 2-[[[(1,1-Dimethylethyl)dimethylsilyl]oxy]methyl]-3-(phenylmethoxy)-1-propanol

HRID 266230Notes

Reaction equation

HRID 266230 reaction equation
[H-].[Na+].[CH2:3]([O:10][CH2:11][CH:12]([CH2:15][OH:16])[CH2:13][OH:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]>CCCCC.C1COCC1.C(OCC)(=O)C>[CH2:3]([O:10][CH2:11][CH:12]([CH2:15][O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH2:13][OH:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chlorideHCID 102417822-benzyloxymethyl-propane-1,3-diol

Product 1

HCID 541774382-[[[(1,1-Dimethylethyl)dimethylsilyl]oxy]methyl]-3-(phenylmethoxy)-1-propanolYield 82%

Reagents, catalysts & solvents 3

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

NaH (0.87 g, 80% dispersion in oil, 29.1 mmol) was washed three times with dry pentane, dried in vacuo, and then suspended in 60 mL of dry THF. A solution of 2-benzyloxymethyl-1,3-propanediol (5.70 g, 29.1 mmol) in 5 mL of THF was next added dropwise over 20 min. and the reaction mixture stirred at room temperature for 1.5 hrs. to give a white slurry. t-Butyldimethylsilylchloride (4.38 g, 29.1 mmol) was then added portionwise over 3 min. and the reaction mixture stirred at room temperature for 2 hours further. The mixture was next diluted with 150 mL of ethyl acetate and washed with 10% aqueous potassium carbonate and brine, dried over MgSO4, filtered, and concentrated to give a colorless oil. Purification by column chromatography on silica gel (ethyl acetate/hexanes) provided 7.41 g (82%) of 2-benzyloxymethyl-3-t-butyldimethylsiloxy-1-propanol as a clear, colorless liquid.

Workup

  1. customdried in vacuo
  2. customto give a white slurry
  3. stirringthe reaction mixture stirred at room temperature for 2 hours further
  4. washwashed with 10% aqueous potassium carbonate and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a colorless oil
  9. customPurification by column chromatography on silica gel (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-af3f094e961a4e33b4b2993c3d008d47
Source dataset
uspto-grants-1997_07
Patent number
US05650510

Reaction notes

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