Triethylamine → 2-[Di(benzyloxy)phosphoryloxy]ethyl 4-nitrophenyl carbonate

HRID 1761238Notes

Reaction equation

HRID 1761238 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:3].[CH2:14]([O:21][P:22]([O:32][CH2:33][CH2:34][OH:35])([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C>ClCCl>[C:2](=[O:3])([O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:11]([O-:13])=[O:12])=[CH:9][CH:10]=1)[O:35][CH2:34][CH2:33][O:32][P:22]([O:21][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 152563952-[Di(benzyloxy)phosphoryloxy]ethanol

Product 1

HCID 213066252-[Di(benzyloxy)phosphoryloxy]ethyl 4-nitrophenyl carbonateYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Nitrophenyl chloroformate (1.01 g; 5.04 mmol) was added at 0° C. under argon atmosphere to a solution of 2-[di(benzyloxy)phosphoryloxy]ethanol (1.62 g; 5.09 mmol) and triethylamine (0.7 ml; 5 mmol) in dichloromethane (20 ml). The mixture was stirred at ambient temperature for 30 minutes, evaporated and purified by flash chromatography, eluting with petroleum ether/ethyl acetate (40/60) to give 2-[di(benzyloxy)phosphoryloxy]ethyl 4-nitrophenyl carbonate.

Workup

  1. customevaporated
  2. custompurified by flash chromatography
  3. washeluting with petroleum ether/ethyl acetate (40/60)

Sources & evidence

ORD record
ord-9f9410e14e5540569dc7ac8cfc75821a
Source dataset
uspto-grants-2005_01
Patent number
US06846925B2

Reaction notes

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