Methanol → HCID 13827615, compound

HRID 235673Notes

Reaction equation

HRID 235673 reaction equation
[CH:1]1([C:6]2([CH3:22])[CH2:14][C:13]3[C:8](=[C:9]([Cl:20])[C:10]([Cl:19])=[C:11]([S:15]C(=O)C)[CH:12]=3)[C:7]2=[O:21])[CH2:5][CH2:4][CH2:3][CH2:2]1.CO.[OH-].[Na+]>O1CCCC1>[CH:1]1([C:6]2([CH3:22])[CH2:14][C:13]3[C:8](=[C:9]([Cl:20])[C:10]([Cl:19])=[C:11]([SH:15])[CH:12]=3)[C:7]2=[O:21])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 13827614(2RS)-2-cyclopentyl-2-methyl-5-acetylthio-6,7-dichloroindan-1-one

Product 1

HCID 13827615HCID 13827615, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 300 mg of 5-acetylthio compound prepared in (2) in the mixture of 1.3 ml of methanol and 0.6 ml of tetrahydrofuran was dropped 1.35 ml of 5% aqueous solution of sodium hydroxide and the mixture was stirred for 20 minutes at ambient and then concentrated under reduced pressure. 2 ml of water was added to the residue and the mixture was acidified to pH 1 with 1N hydrochloric acid under cooled with ice. The mixture was extracted with diethyl ether and the extract was washed successively with water and a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to give 210 mg of the title compound as crude product having following physical data.

Workup

  1. concentrationthen concentrated under reduced pressure
  2. addition2 ml of water was added to the residue
  3. temperatureunder cooled with ice
  4. extractionThe mixture was extracted with diethyl ether
  5. washthe extract was washed successively with water
  6. dry with materiala saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-efa39192862145bb9f1832c1ccfa7d31
Source dataset
uspto-grants-1987_02
Patent number
US04640931

Reaction notes

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