Acetonitrile → HCID 20285729, compound

HRID 460988Notes

Reaction equation

HRID 460988 reaction equation
[CH3:1][C:2]1[S:3][C:4]([S:10][CH3:11])=[C:5]([CH3:9])[C:6]=1[CH2:7]O.[Br-:12].[C:13]1([PH+:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(#N)C.C(OCC)(=O)C>C(OCC)C.CCCCCC>[Br-:12].[CH3:1][C:2]1[S:3][C:4]([S:10][CH3:11])=[C:5]([CH3:9])[C:6]=1[CH2:7][P+:19]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8857Ethyl AcetateHCID 517696Phosphine, triphenyl-, hydrobromideHCID 20285713HCID 20285713, compound

Product 1

HCID 20285729HCID 20285729, compound

Reagents, catalysts & solvents 1

HCID 21584099Diethylether hexaneSolvent

Procedure

14.0 G. of 2,4-dimethyl-3-hydroxymethyl-5-(methylthio)thiophene and 26.0 G. of triphenylphosphonium bromide were dissolved in 75 ml. of acetonitrile and stirred at 40° C. for 1 hour. The resulting mixture was cooled and poured into 150 ml. of ethyl acetate then treated with ethyl ether/hexane (5:1). The resulting solution was decanted from a gum-like residue. The residue was treated with hot acetone and the resulting whitecrystals were filtered, washed with cold acetone and dried under high vacuum at 80° C. to yield [2,4-dimethyl-5-(methylthio)-3-thenyl]triphenylphosphonium bromide, m.p. 245°-248° C.

Workup

  1. temperatureThe resulting mixture was cooled
  2. additionpoured into 150 ml
  3. customThe resulting solution was decanted from a gum-like residue
  4. additionThe residue was treated with hot acetone
  5. filtrationthe resulting whitecrystals were filtered
  6. washwashed with cold acetone
  7. customdried under high vacuum at 80° C.

Sources & evidence

ORD record
ord-bcaa97ab41f4483796f714c81ca1658b
Source dataset
uspto-grants-1977_12
Patent number
US04061656

Reaction notes

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