Dimethylformamide → HCID 19913071, compound

HRID 1089174Notes

Reaction equation

HRID 1089174 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)=[CH2:12])[CH2:10][O:9]2)=[CH:4][CH:3]=1.N1C=[CH:23][N:22]=[N:21]1.[K].[CH3:26][N:27](C=O)C>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:9])([C:11]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[CH2:12])[CH2:10][N:22]2[CH:23]=[N:27][CH:26]=[N:21]2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 19913058HCID 19913058, compoundHCID 178506621HCID 178506621, compound

Product 1

HCID 19913071HCID 19913071, compound

Procedure

A mixture of 10.2 g (0.040 mol) of crude 2-(4-fluorophenyl)-2-[1-(4-fluorophenyl)ethenyl]oxirane and 7.0 g (0.065 mol) of potassium triazole in 60 mL of DMF was heated at 60° overnight then cooled and poured into 100 mL of 1:1 Et2O/hexanes. After washing the organic layer three times with H2O and once with brine, a precipitate formed in the organic layer. Filtering gave 4.8 g of a brown solid which was recrystallized from 500 mL of cyclohexane to yield 2.5 g of a light-tan powder, mp 136°-137°: NMR (CDCl3) δ 1.7 (br s, OH); 4.7 (q, 2H); 5.3 (s, 1H); 5.5 (s, 1H); 6.8-7.1 (m, 6H); 7.4 (m, 2H); 7.8 (s, 1H); 7.9 (s, 1H); IR (nujol) 3120 (br, 1900, 1600, 1505, 1220, 1139, 835 cm-1.

Workup

  1. temperaturewas heated at 60° overnight
  2. temperaturethen cooled
  3. washAfter washing the organic layer three times with H2O
  4. customonce with brine, a precipitate formed in the organic layer
  5. filtrationFiltering

Sources & evidence

ORD record
ord-44743107a6d14edb9732039d5eb4a57c
Source dataset
uspto-grants-1990_10
Patent number
US04965280

Reaction notes

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