3-Bromo-1-propanol → Phosphoric acid di-tert-butyl ester 3-hydroxy-propyl ester

HRID 585154Notes

Reaction equation

HRID 585154 reaction equation
[C:1]([O:5][P:6](=[O:13])([O-:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2].C([N+](CCCC)(CCCC)CCCC)CCC.Br[CH2:32][CH2:33][CH2:34][OH:35]>COCCOC>[OH:35][CH2:34][CH2:33][CH2:32][O:13][P:6](=[O:12])([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 123083-Bromo-1-propanolHCID 22339116Tetra-n-butylammonium di-tert-butylphosphate

Product 1

HCID 85869323Phosphoric acid di-tert-butyl ester 3-hydroxy-propyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a 100 mL flask was added tetra-n-butyl ammonium phosphoric acid di-tert-butyl ester salt (3.08 g, 6.8 mmol), ethylene glycol dimethyl ether (10 mL), and 3-bromo-1-propanol (freshly distilled from potassium carbonate). The reaction mixture was heated to reflux for 2.5 hours. After cooling to room temperature, the reaction mixture was diluted with ethyl ether (60 mL) and cooled in a refrigerator until a white solid precipitated. The solid was filtered through Celite and the filtrate was evaporated in vacuo, affording the title compound as a clear oil (1.85 g, ˜100%). 1H NMR (CDCl3, 500 MHz) δ 4.10 (m, 2H), 3.73 (m, 2H), 1.84 (m, 2H), 1.46 (s, 18H).

Workup

  1. distillationfreshly distilled from potassium carbonate)
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux for 2.5 hours
  4. additionthe reaction mixture was diluted with ethyl ether (60 mL)
  5. temperaturecooled in a refrigerator until a white solid
  6. customprecipitated
  7. filtrationThe solid was filtered through Celite
  8. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-eb764b8c137c4d0db462103c93857ca7
Source dataset
uspto-grants-2005_08
Patent number
US06930100B2

Reaction notes

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