Trimethyl phosphite → HCID 14877956, compound

HRID 1085749Notes

Reaction equation

HRID 1085749 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-649080c2f4fb41bdbfb783699dd5275a
Source dataset
uspto-grants-1991_04
Patent number
US05010205

Reaction notes

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