Thionyl Chloride → HCID 20144476, compound

HRID 649018Notes

Reaction equation

HRID 649018 reaction equation
O[CH2:2][C:3]1[C:4]2[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:5]=2[S:6][CH:7]=1.O=S(Cl)[Cl:15]>CCOCC>[Cl:15][CH2:2][C:3]1[C:4]2[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:5]=2[S:6][CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 601251HCID 601251, compound

Product 1

HCID 20144476HCID 20144476, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

290 mg of 3-hydroxymethyl-7-methyl-benzo[b]thiophene are dissolved in ether, 0.6 ml SOCl2 added and the mixture stirred for 2 hours at room temperature. The reaction mixture is poured onto ice and the organic phase washed neutral, dried and concentrated under vacuum. The crude 3-chloromethyl-7-methyl-benzothiophene thus obtained is dissolved in acetone, mixed with an aqueoug solution of 170 mg of KCN and refluxed for 18 hours. The reaction mixture is concentrated, the residue partitioned between water and ether and the organic phase washed, dried, concentrated and chromatographed over silica-gel (eluant: toluene) to yield the title product is an oil.

Workup

  1. additionThe reaction mixture is poured onto ice
  2. washthe organic phase washed neutral
  3. customdried
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-41e9e4aff8bb42cf9c84054c5d2d96bb
Source dataset
uspto-grants-1988_04
Patent number
US04737516

Reaction notes

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