Triethylamine → 2-n-Heptylthio-4-tetrahydropyranyloxycyclopent-2-en-1-one

HRID 1448633Notes

Reaction equation

HRID 1448633 reaction equation
O1[CH:6]2[CH:2]1[C:3](=[O:14])[CH2:4][CH:5]2[O:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][O:9]1.[CH2:15]([SH:22])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].C(N(CC)CC)C.[Cl-].[NH4+]>CO>[CH2:15]([S:22][C:2]1[C:3](=[O:14])[CH2:4][CH:5]([O:7][CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][O:9]2)[CH:6]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 154221-HeptanethiolHCID 25517Ammonium ChlorideHCID 203803472,3-Epoxy-4-(2-tetrahydropyranyloxy)cyclopentan-1-one

Product 1

HCID 203803622-n-Heptylthio-4-tetrahydropyranyloxycyclopent-2-en-1-oneYield 28%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2,3-Epoxy-4-tetrahydropyranyloxycyclopentan-1-one (200 mg) and 121 mg of n-heptylmercaptan were dissolved in 5 ml of methanol, and 158 mg of triethylamine was added. The mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into an aqueous solution of ammonium chloride, and extracted with ethyl acetate. The extract was treated by a customary procedure to afford 280 mg of a crude product. The crude product was chromatographed on a thin layer plate with cyclohexane/ethyl acetate (=6/4) to afford 80 mg of 2-n-heptylthio-4-tetrahydropyranyloxycyclopent-2-en-1-one in a yield of 26%. The product had the following characteristics.

Workup

  1. extractionextracted with ethyl acetate
  2. additionThe extract was treated by a customary procedure
  3. customto afford 280 mg of a crude product
  4. customThe crude product was chromatographed on a thin layer plate with cyclohexane/ethyl acetate (=6/4)

Sources & evidence

ORD record
ord-6898734ac18841669266e37710825132
Source dataset
uspto-grants-1979_12
Patent number
US04180672

Reaction notes

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