Triethylamine → Tert-butyl (diphenoxyphosphoryl)acetate

HRID 394206

Reaction equation

HRID 394206 reaction equation
[C:1]1([O:7][P:8]([O-:16])[O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17]([O:21][C:22](=[O:25])[CH2:23]Br)([CH3:20])([CH3:19])[CH3:18].C(N(CC)CC)C>ClCCl>[O:9]([P:8]([CH2:23][C:22]([O:21][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:25])([O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:16])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 79177tert-Butyl bromoacetateHCID 23418553Diphenoxyphosphanolate

Product 1

HCID 10689048Tert-butyl (diphenoxyphosphoryl)acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of diphenylphosphite (2.25 mL) in dichloromethane at 0° C. was added t-butylbromoacetate (1.48 mL) followed by triethylamine (1.95 mL). The mixture was stirred at 0° C. for 15 min and then at rt for 1 h before being quenched with water and extracted into ethyl acetate, dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography eluting with hexane/ethyl acetate to give the title compound. 1H NMR (500 MHz, CDCl3): δ 7.40-7.18 (m, 10H); 3.22 (s, 1H); 3.18 (s, 1H); 1.50 (s, 9H).

Workup

  1. customat rt for 1 h before being quenched with water
  2. extractionextracted into ethyl acetate
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with hexane/ethyl acetate

Sources & evidence

ORD record
ord-65ac710e789949a5880f74f2b654d1e1
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Linked notes

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