Trimethyl phosphite → HCID 14877956, compound

HRID 1460341Notes

Reaction equation

HRID 1460341 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)=[C:9]([N:12]2[CH:16]=[N:15][N:14]=[N:13]2)[CH2:10]Br)=[CH:4][CH:3]=1.[CH3:24][O:25][P:26]([O:29]C)[O:27][CH3:28]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)=[C:9]([N:12]2[CH:16]=[N:15][N:14]=[N:13]2)[CH2:10][P:26](=[O:29])([O:27][CH3:28])[O:25][CH3:24])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 8472Trimethyl phosphiteHCID 15678619HCID 15678619, compound

Product 1

HCID 14877956HCID 14877956, compoundYield 83.2%

Procedure

A suspension of 3,3-bis(4-fluorophenyl)-1-bromo-2-(tetrazol-1-yl)-2-propene (108 mg, 0.29 mmol) and trimethylphosphite (4 mL, 34 mmol) was heated to reflux under an inert atmosphere for five minutes. After cooling to room temperature, excess trimethylphosphite was evaporated under reduced pressure to give a pale crystalline material. The crude product was crystallized from a 10:1 mixture of hexanes: ethyl acetate to give 98 mg (83%) of the title compound as rhombic, colorless crystals; m.p.=132.8°-133.7° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under an inert atmosphere for five minutes
  3. customexcess trimethylphosphite was evaporated under reduced pressure
  4. customto give a pale crystalline material
  5. customThe crude product was crystallized from a 10:1 mixture of hexanes

Sources & evidence

ORD record
ord-26af40d564114e62badadb4364b80c23
Source dataset
uspto-grants-1991_12
Patent number
US05070206

Reaction notes

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