Sodium Bicarbonate → 4-Hydroxy-2-n-octylthiocyclopent-2-en-1-one

HRID 1448631Notes

Reaction equation

HRID 1448631 reaction equation
[O:1]([CH:9]1[CH2:13][C:12](=[O:14])[C:11]([S:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:10]1)[Si](C(C)(C)C)(C)C.C(=O)(O)[O-].[Na+]>C(O)(=O)C.O.O1CCCC1>[OH:1][CH:9]1[CH2:13][C:12](=[O:14])[C:11]([S:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:10]1

Participants

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 203803744-t-Butyldimethylsiloxy-2-n-octylthiocyclopent-2-en-1-one

Product 1

HCID 127679754-Hydroxy-2-n-octylthiocyclopent-2-en-1-oneYield 84%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-t-Butyldimethylsiloxy-2-n-octylthiocyclopent-2-en-1-one (90 mg) was dissolved in 5 ml of a mixture of acetic acid, water and tetrahydrofuran in a ratio of 3:1:1, and reacted at room temperature for 48 hours. The reaction mixture was neutralized with sodium bicarbonate, and extracted with ethyl acetate. The extract was treated by conventional methods, and chromatographed on a thin layer plate with cyclohexane/ethyl acetate (4/6) to afford 48 mg of 4-hydroxy-2-n-octylthiocyclopent-2-en-1-one in a yield of 84% showing a single spot. The resulting product had the following characteristics.

Workup

  1. customreacted at room temperature for 48 hours
  2. extractionextracted with ethyl acetate
  3. additionThe extract was treated by conventional methods
  4. customchromatographed on a thin layer plate with cyclohexane/ethyl acetate (4/6)

Sources & evidence

ORD record
ord-af5046921eea42b39262e19ab318d181
Source dataset
uspto-grants-1979_12
Patent number
US04180672

Reaction notes

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