Sodium Hydroxide → HCID 20380421, compound

HRID 1448638Notes

Reaction equation

HRID 1448638 reaction equation
[C:1]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][S:10][C:11]1[C:12](=[O:16])[CH2:13][CH2:14][CH:15]=1)([O:3]C)=[O:2].[OH-].[Na+]>CO.O>[C:1]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][S:10][C:11]1[C:12](=[O:16])[CH2:13][CH2:14][CH:15]=1)([OH:3])=[O:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 19607074Methyl 6-[(5-oxocyclopent-1-en-1-yl)sulfanyl]hexanoate

Product 1

HCID 20380421HCID 20380421, compoundYield 51.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2-(5-Carbomethoxypentylthio)cyclopent-2-en-1-one (133 mg) was treated with 0.8 ml of a 3 N aqueous solution of sodium hydroxide in 5 ml of methanol and 2 ml of water at room temperature for 45 minutes. After the reaction, the reaction mixture was extracted with diethyl ether. The aqueous layer was acidified with hydrochloric acid, and extracted with diethyl ether. The extracts were treated in a customary manner to afford 125 mg of a crude product. The crude product was chromatographed on a thin layer plate with diethyl ether/isopropyl ether/acetic acid (=75/30/3) to afford 65 mg of 2-(5-carboxypentylthio)cyclopent-2-en-1-one in a yield of 49%. The product had the following characteristics.

Workup

  1. customAfter the reaction
  2. extractionthe reaction mixture was extracted with diethyl ether
  3. extractionextracted with diethyl ether
  4. additionThe extracts were treated in a customary manner
  5. customto afford 125 mg of a crude product
  6. customThe crude product was chromatographed on a thin layer plate with diethyl ether/isopropyl ether/acetic acid (=75/30/3)

Sources & evidence

ORD record
ord-8b6cb305f15d46079e63592f8605257b
Source dataset
uspto-grants-1979_12
Patent number
US04180672

Reaction notes

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