Triethylamine → HCID 20404787, compound

HRID 2164582Notes

Reaction equation

HRID 2164582 reaction equation
[CH2:1]([S:4][CH:5]1[CH2:11][CH:10]2[CH:7]([C:8](=[O:12])[CH2:9]2)[CH:6]1[C:13]([O:15][CH3:16])=[O:14])[CH2:2][CH3:3].S(Cl)(Cl)(=O)=O.C(N(CC)CC)C>C(Cl)Cl>[CH2:1]([S:4][C:5]1[CH2:11][CH:10]2[CH:7]([C:8](=[O:12])[CH2:9]2)[C:6]=1[C:13]([O:15][CH3:16])=[O:14])[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24648Sulfuryl chlorideHCID 20404808HCID 20404808, compound

Product 1

HCID 20404787HCID 20404787, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 33 mg of crude methyl 3-(1-propylthio)-7-oxobicyclo[3.2.0]heptan-2-carboxylate, prepared by the procedure of Paragraph A, in 2 mL of methylene chloride at -40° under argon was added 24 mg of sulfuryl chloride. This solution was stirred for 15 min at -40° and then cooled to -70°. Triethylamine was added until the solution was basic to pH paper, and the solution was allowed to warm slowly to room temperature. The reaction mixture was partitioned between methylene chloride and brine, and the organic layer was dried over sodium sulfate and concentrated to dryness. The crude product was purified by preparative thin layer chromatography on three 20×10×0.05 cm silica gel plates, eluting with ether-petroleum ether (1:1), to afford after crystallization from ether 7.5 mg (23%) of methyl 3-(1-propylthio)-7-oxobicyclo[3.2.0]hept-2-en-2-carboxylate: NMR (220 MHz; CDCl3): δ 1.05 (3 H, t, J=7), 1.68 (2H, m), 2.87 (2H, t, J=7), 2.9-3.0 (3H, m), 3.3-3.45 (2H, m), 3.78 (3H, s), and 4.51 (1H, m); HRMS: Calcd for C12H16O3S, 240.0819; found, 240.0807.

Workup

  1. temperaturecooled to -70°
  2. customThe reaction mixture was partitioned between methylene chloride and brine
  3. dry with materialthe organic layer was dried over sodium sulfate
  4. concentrationconcentrated to dryness
  5. customThe crude product was purified by preparative thin layer chromatography on three 20×10×0.05 cm silica gel plates
  6. washeluting with ether-petroleum ether (1:1)
  7. customto afford
  8. customafter crystallization from ether 7.5 mg (23%) of methyl 3-(1-propylthio)-7-oxobicyclo[3.2.0]hept-2-en-2-carboxylate

Sources & evidence

ORD record
ord-a934a65bcdeb4332bbb3cf73134d0280
Source dataset
uspto-grants-1985_03
Patent number
US04505905

Reaction notes

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