Sodium Bicarbonate → (R)-3-Benzyloxy-1-tetradecanol

HRID 233472Notes

Reaction equation

HRID 233472 reaction equation
[CH2:1]([O:8][C@H:9]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:10][CH2:11][O:12][Si](C(C)(C)C)(C)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+]>C(#N)C>[CH2:1]([O:8][C@H:9]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:10][CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 53803651(R)-3-Benzyloxy-1-tert-butyl-dimethylsiloxytetradecane

Product 1

HCID 11723551(R)-3-Benzyloxy-1-tetradecanolYield 73.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of aqueous HF (50%, 12 mL) was added to a mixture of compound 45 (6.3 g, 14.5 mmol) in acetonitrile (120 mL) and the mixture was stirred for 30 min. After completion of the reaction, the acid was neutralized with saturated sodium bicarbonate solution and extracted with ethyl acetate (3×150 mL) and the organic phase was separated, dried, concentrated, and the product was purified by flash chromatography to afford compound 46 as colorless oil (Rf 0.42, 25% ethyl acetate in hexane, 3.4 g, 74%).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate (3×150 mL)
  3. customthe organic phase was separated
  4. customdried
  5. concentrationconcentrated
  6. customthe product was purified by flash chromatography

Sources & evidence

ORD record
ord-f7c94b3f81e24d839b4bafb32303f466
Source dataset
uspto-grants-1997_01
Patent number
US05593969

Reaction notes

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