Water → ethyl 4-oxo-5,6,7,8-tetrahydro-4H-cyclohepta[b]furan-3-carboxylate

HRID 1290086Notes

Reaction equation

HRID 1290086 reaction equation
CS(Cl)(=O)=O.O[C:7]1([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:11][O:10][C:9]2[CH2:12][CH2:13][CH2:14][CH2:15][C:16](=[O:17])[C:8]1=2.C(N(CC)CC)C.O>ClCCl>[O:17]=[C:16]1[C:8]2[C:7]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:11][O:10][C:9]=2[CH2:12][CH2:13][CH2:14][CH2:15]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 18696566ethyl 3-hydroxy-4-oxo-2,3,5,6,7,8-hexahydro-4H-cyclohepta[b]furan-3-carboxylate

Product 1

HCID 18696560ethyl 4-oxo-5,6,7,8-tetrahydro-4H-cyclohepta[b]furan-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (9.7 g, 0.08 mol) was added dropwise to a stirring solution of ethyl 3-hydroxy-4-oxo-2,3,5,6,7,8-hexahydro-4H-cyclohepta[b]furan-3-carboxylate (17 g, 0.07 mol) and triethylamine (30 mL, 0.21 mol) in dichloromethane (100 mL) at 0° C. The mixture was allowed to reach ambient temperature, stirred for 2 hours, then poured into water and extracted with dichloromethane. The organic layer was washed sequentially with aqueous 2N sodium hydroxide, saturated aqueous sodium bicarbonate, and brine, then dried over magnesium sulfate, filtered, concentrated in vacuo, and purified on Silica gel (1:1 ethyl acetate/hexanes) to give the title compound.

Workup

  1. customto reach ambient temperature
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed sequentially with aqueous 2N sodium hydroxide, saturated aqueous sodium bicarbonate, and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified on Silica gel (1:1 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-085c137279374d3d9603603b96207c47
Source dataset
uspto-grants-1998_05
Patent number
US05750702

Reaction notes

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