Chloride → HCID 57294516, compound

HRID 1701506Notes

Reaction equation

HRID 1701506 reaction equation
O[C:2]1([CH:14]=[CH2:15])[C:11]2([CH3:12])[C:6](=[CH:7][C:8](=[O:13])[CH2:9][CH2:10]2)[CH:5]=[CH:4][CH2:3]1.S(Cl)([Cl:18])=O.C(=O)(O)[O-].[Na+].[Cl-]>C(Cl)Cl.O.N1C=CC=CC=1>[Cl:18][CH2:15][CH:14]=[C:2]1[C:11]2([CH3:12])[C:6](=[CH:7][C:8](=[O:13])[CH2:9][CH2:10]2)[CH:5]=[CH:4][CH2:3]1

Participants

8

Reactant 4

HCID 312ChlorideHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 20341182HCID 20341182, compound

Product 1

HCID 57294516HCID 57294516, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-hydroxy-8a-methyl-1-vinyl-1,2,6,7,8,8a-hexahydro-6-naphthalenone (0.204 g.) in anhydrous methylene chloride (20 ml.) was added 0.5 ml. of pyridine. The reaction mixture was cooled in an ice-bath and thionyl chloride (150 mg.) was added. After 5 minutes, the reaction mixture was diluted with methylene chloride (20 ml.) and water (10 ml.) and neutralized with saturated sodium bicarbonate solution (5 ml.). The aqueous layer was extracted with methylene chloride (3×25 ml.) and the combined organic layers were washed with brine and dried over sodium sulfate. Evaporation of solvent gave 217 mg. of the oily chloride.

Workup

  1. temperatureThe reaction mixture was cooled in an ice-bath
  2. extractionThe aqueous layer was extracted with methylene chloride (3×25 ml.)
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. customEvaporation of solvent
  6. customgave 217 mg

Sources & evidence

ORD record
ord-3d5c8da23ce44ad8b72b220a7eb70f20
Source dataset
uspto-grants-1980_03
Patent number
US04193940

Reaction notes

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