Pyridine → HCID 19883488, compound

HRID 35305Notes

Reaction equation

HRID 35305 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:17][CH2:18][CH2:19]O)[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][O:9]2)=[CH:4][CH:3]=1.N1C=CC=CC=1.S(Cl)([Cl:29])=O>ClC(Cl)Cl>[Cl:29][CH2:19][CH2:18][CH2:17][C:8]1([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][O:9]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 198835271-(4-Fluorophenyl)-1,3-dihydroisobenzofuran-1-propanol

Product 1

HCID 19883488HCID 19883488, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 24.2 parts of 1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-propanol in 8 parts of pyridine and 90 parts of trichloromethane were added dropwise 12.1 parts of thionyl chloride. Upon completion, the whole was heated slowly to 50° C. and stirring at this temperature was continued for 3 hours. The reaction mixture was poured onto ice-water. The organic phase was separated, washed with a sodium hydrogen carbonate solution (10%), dried and evaporated, yielding 20 parts of 1-(3-chloropropyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran as a residue (intermediate 12).

Workup

  1. additionThe reaction mixture was poured onto ice-water
  2. customThe organic phase was separated
  3. washwashed with a sodium hydrogen carbonate solution (10%)
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-fe67d16fd2484218ba950edb3088cd79
Source dataset
uspto-grants-1988_08
Patent number
US04766125

Reaction notes

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