Sodium hydride → HCID 10754259, compound

HRID 1737456Notes

Reaction equation

HRID 1737456 reaction equation
[H-].[Na+].[C:3]1([CH:9]([CH2:12][OH:13])[CH2:10][OH:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]>C1COCC1>[C:3]1([CH:9]([CH2:10][O:11][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:12][OH:13])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chlorideHCID 2541782-Phenyl-1,3-propanediol

Product 1

HCID 10754259HCID 10754259, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% dispersion in mineral oil, 525 mg, 13 mmol) was added to a round bottom flask and washed with 3×5 mL of dry hexane. Dry THF (25 mL) was then added, followed by 2-phenyl-1,3-propanediol (2.0 g, 13 mmol). Another 25 mL of dry THF was added to facilitate stirring of the resulting thick suspension. After 45 min., tert-butyldimethylsilyl chloride was added in one portion. After stirring for 2 h, the mixture was partitioned between 100 mL of ethyl ether and 60 mL of 10% aqueous potassium carbonate. The aqueous layer was extracted with 2×30 mL of ethyl ether. The combined organic layers were washed with 40 mL of brine, dried over sodium sulfate, and evaporated. Purification by flash column chromatography, eluting with 10% ethyl acetate in hexane, gave the 3.36 g of the title compound as a colorless liquid. 1NMR (400 MHz,CD3OD): δ 7.30-7.16(m, 5H), 3.90 (dd, 1H, J=11, 7 Hz), 3.88 (dd, 1H, J=10, 6 Hz), 3.83 (dd, 1H, J=10, 6 Hz), 3.76 (dd, 1H, J=11, 7 Hz), 2.91 (quintet, 1H, J=6 Hz), 0.84 (s, 9H),-0.04 (s, 3H),-0.05 (s, 3H). Mass spectrum (NH3 /CI): m/z=267 (M+1).

Workup

  1. washwashed with 3×5 mL of dry hexane
  2. additionDry THF (25 mL) was then added
  3. stirringAfter stirring for 2 h
  4. customthe mixture was partitioned between 100 mL of ethyl ether and 60 mL of 10% aqueous potassium carbonate
  5. extractionThe aqueous layer was extracted with 2×30 mL of ethyl ether
  6. washThe combined organic layers were washed with 40 mL of brine
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customPurification by flash column chromatography
  10. washeluting with 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-41a189b7a78a453c9df8ef3df7003354
Source dataset
uspto-grants-1999_10
Patent number
US05962462

Reaction notes

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