Triethyl phosphite → (5-t-Butyl-oxazol-2-ylmethyl)-phosphonic acid diethyl ester

HRID 2085367Notes

Reaction equation

HRID 2085367 reaction equation
Cl[CH2:2][C:3]1[O:4][C:5]([C:8]([CH3:11])([CH3:10])[CH3:9])=[CH:6][N:7]=1.[CH2:12]([O:14][P:15]([O:19]CC)[O:16][CH2:17][CH3:18])[CH3:13]>C1(C)C=CC=CC=1>[CH2:12]([O:14][P:15]([CH2:2][C:3]1[O:4][C:5]([C:8]([CH3:11])([CH3:10])[CH3:9])=[CH:6][N:7]=1)(=[O:19])[O:16][CH2:17][CH3:18])[CH3:13]

Participants

4

Reactant 2

HCID 31215Triethyl phosphiteHCID 129689745-tert-Butyl-2-(chloromethyl)-1,3-oxazole

Product 1

HCID 11033086(5-t-Butyl-oxazol-2-ylmethyl)-phosphonic acid diethyl esterYield 98%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-(chloromethyl)-5-t-butyloxazole (8.00 g, 46.1 mmol) in triethylphosphite (15.3 g, 92.0 mmol) was heated at 120° C. for 18 hours. After cooling the mixture to room temperature, toluene (30 mL) was added and the solution was concentrated in vacuo with a bath temperature of 70° C. This procedure was repeated three times and the resulting brown oil was dried in vacuo at 90° C. for 30 minutes to give (5-t-butyl-oxazol-2-ylmethyl)-phosphonic acid diethyl ester (12.4 g, 98%, C12H22NO4P, MS m/e 276 (M+H)+) as a red-orange liquid.

Workup

  1. concentrationthe solution was concentrated in vacuo with a bath temperature of 70° C
  2. customthe resulting brown oil was dried in vacuo at 90° C. for 30 minutes

Sources & evidence

ORD record
ord-8d90cb55eb67496fbd7d331799146240
Source dataset
uspto-grants-2004_04
Patent number
US06720347B2

Reaction notes

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