Sodium Bicarbonate → 2-n-Heptylthio-4-hydroxycyclopent-2-en-1-one

HRID 1448634Notes

Reaction equation

HRID 1448634 reaction equation
[CH2:1]([S:8][C:9]1[C:10](=[O:21])[CH2:11][CH:12]([O:14]C2CCCCO2)[CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].C(=O)(O)[O-].[Na+].C1CCCCC1.C(OCC)(=O)C>C(O)(=O)C.O.O1CCCC1>[CH2:1]([S:8][C:9]1[C:10](=[O:21])[CH2:11][CH:12]([OH:14])[CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 203803622-n-Heptylthio-4-tetrahydropyranyloxycyclopent-2-en-1-oneHCID 21867204Cyclohexane ethylacetate

Product 1

HCID 203803872-n-Heptylthio-4-hydroxycyclopent-2-en-1-oneYield 99.2%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-n-Heptylthio-4-tetrahydropyranyloxycyclopent-2-en-1-one (80 mg) was dissolved in 5 ml of a mixture of acetic acid, water and tetrahydrofuran in a ratio of 3:1:1 and 2 ml of acetic acid, and the solution was allowed to stand at room temperature for 12 hours. The reaction mixture was neutralized with sodium bicarbonate, and extracted with ethyl acetate. The extract was treated by a customary procedure to afford 58 mg (95% yield) of 2-n-heptylthio-4-hydroxycyclopent-2-en-1-one having a single spot in thin-layer chromatography (cyclohexane/ethyl acetate=4/6). The product had the following characteristics.

Workup

  1. extractionextracted with ethyl acetate
  2. additionThe extract was treated by a customary procedure

Sources & evidence

ORD record
ord-5f0dfdb5ae0b429abecec7d8bcda2a1e
Source dataset
uspto-grants-1979_12
Patent number
US04180672

Reaction notes

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