Ethyl Acetate → HCID 131734119, compound

HRID 1508637Notes

Reaction equation

HRID 1508637 reaction equation
[H-].[Na+].[CH2:3]([O:10][CH2:11][CH:12]([OH:17])[CH2:13][CH2:14][CH2:15][OH:16])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH:18]([Si:21](Cl)([CH:25]([CH3:27])[CH3:26])[CH:22]([CH3:24])[CH3:23])([CH3:20])[CH3:19].C(OCC)(=O)C>O1CCCC1.O>[CH2:3]([O:10][CH2:11][CH:12]([OH:17])[CH2:13][CH2:14][CH2:15][O:16][Si:21]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[CH:18]([CH3:20])[CH3:19])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 139400Triisopropylsilyl chlorideHCID 13181689HCID 13181689, compound

Product 1

HCID 131734119HCID 131734119, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.96 g of sodium hydride (60 wt % in oil) was added to a solution of 5.0 g of 5-(benzyloxy)pentane-1,4-diol in 50 mL of tetrahydrofuran in a nitrogen atmosphere at a temperature of 5° C. to 10° C., and the obtained mixture was then stirred at room temperature for 30 minutes. Thereafter, 5.3 mL of triisopropylsilyl chloride was added dropwise to the reaction mixture at a temperature of 5° C. to 10° C. The reaction mixture was stirred at room temperature for 1 hour, and it was then added to a mixture of 100 mL of ethyl acetate and 100 mL of water. The organic layer was fractionated. The obtained organic layer was successively washed with 100 mL of a saturated sodium hydrogen carbonate aqueous solution, 100 mL of water and 100 mL of a saturated sodium chloride aqueous solution, and it was then dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure, and the obtained residue was then purified by silica gel column chromatography (ethyl acetate/hexane=1/5 to 1/5), so as to obtain 5.4 g of 1-benzyloxy-5-((triisopropyl)silyloxy)pentan-2-ol in the form of a colorless oily product.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 1 hour
  2. washThe obtained organic layer was successively washed with 100 mL of a saturated sodium hydrogen carbonate aqueous solution, 100 mL of water and 100 mL of a saturated sodium chloride aqueous solution, and it
  3. dry with materialwas then dried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled away under reduced pressure
  5. customthe obtained residue was then purified by silica gel column chromatography (ethyl acetate/hexane=1/5 to 1/5)

Sources & evidence

ORD record
ord-0c08088f533343c0a1e22beeb3426532
Source dataset
uspto-grants-2015_12
Patent number
US09221865B2

Reaction notes

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