Triethyl phosphite → 3-(Diethoxyphosphorylmethyl)-2-methyl-7-nitrobenzo[b]furan

HRID 342438Notes

Reaction equation

HRID 342438 reaction equation
Cl[CH2:2][C:3]1[C:4]2[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:5]=2[O:6][C:7]=1[CH3:8].[P:16]([O:23]CC)([O:20][CH2:21][CH3:22])[O:17][CH2:18][CH3:19]>>[CH2:18]([O:17][P:16]([CH2:2][C:3]1[C:4]2[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:5]=2[O:6][C:7]=1[CH3:8])([O:20][CH2:21][CH3:22])=[O:23])[CH3:19]

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 701999963-Chloromethyl-2-methyl-7-nitrobenzo[b]furan

Product 1

HCID 867535583-(Diethoxyphosphorylmethyl)-2-methyl-7-nitrobenzo[b]furan

Conditions

Temperature
100 °C

Procedure

A mixture of 3-chloromethyl-2-methyl-7-nitrobenzo[b]furan (226 mg) and triethyl phosphite (0.52 ml) was stirred at 100° C. for 6 hours. The reaction mixture was cooled and concentrated in vacuo and to the residue was added toluene. The mixture was concentrated in vacuo and the residue was purified by column chromatography on silica gel. The obtained oil was crystallized from diisopropyl ether to give 3-(diethoxyphosphorylmethyl)-2-methyl-7-nitrobenzo[b]furan (93 mg).

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated in vacuo and to the residue
  3. additionwas added toluene
  4. concentrationThe mixture was concentrated in vacuo
  5. customthe residue was purified by column chromatography on silica gel
  6. customThe obtained oil was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-e39ccea6228b4abea85e5aa527f9fc5b
Source dataset
uspto-grants-1999_01
Patent number
US05858995

Reaction notes

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