Thionyl Chloride → (+)-(6,7-dichloro-2-cyclopentyl-2,3-dihydro-2-methyl-1-oxo-1H-inden-5-yl)acetyl chloride

HRID 364340Notes

Reaction equation

HRID 364340 reaction equation
[Cl:1][C:2]1[C:10]([Cl:11])=[C:9]2[C:5]([CH2:6][C:7]([CH:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)([CH3:13])[C:8]2=[O:12])=[CH:4][C:3]=1[CH2:19][C:20]([OH:22])=O.S(Cl)([Cl:25])=O>C(Cl)(Cl)Cl.CN(C)C=O>[Cl:1][C:2]1[C:10]([Cl:11])=[C:9]2[C:5]([CH2:6][C:7]([CH:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)([CH3:13])[C:8]2=[O:12])=[CH:4][C:3]=1[CH2:19][C:20]([Cl:25])=[O:22]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 12540263(+)-(6,7-dichloro-2-cyclopentyl-2,3-dihydro-2-methyl-1-oxo-1H-inden-5-yl)acetic acid

Product 1

HCID 13753999(+)-(6,7-dichloro-2-cyclopentyl-2,3-dihydro-2-methyl-1-oxo-1H-inden-5-yl)acetyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of (+)-(6,7-dichloro-2-cyclopentyl-2,3-dihydro-2-methyl-1-oxo-1H-inden-5-yl)acetic acid (21.8 g., 0.0623 mole) in chloroform (150 ml) and dimethylformamide (1 drop) is added thionyl chloride (25 ml). The reaction mixture is heated at reflux for 3 hours, cooled and concentrated at reduced pressure. The crude (+)-(6,7-dichloro-2-cyclopentyl-2,3-dihydro-2-methyl-1-oxo-1H-inden-5-yl)acetyl chloride, thus obtained, is dissolved in methylene chloride (75 ml) and added over 0.5 hour to a mixture of ether (100) ml) and methylene chloride (75 ml) which has been saturated with ammonia.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 3 hours
  3. temperaturecooled
  4. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-696e765d7dd84bcfac8ba58b6ada5e12
Source dataset
uspto-grants-1986_08
Patent number
US04604403

Reaction notes

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