Sulfuric Acid → 5-(Carbomethoxy)-2,4,5,6-tetrahydrocyclopenta[c]furan

HRID 2395996Notes

Reaction equation

HRID 2395996 reaction equation
[C:1]([CH:4]1[CH2:11][C:7]2=[CH:8][O:9][CH:10]=[C:6]2[CH2:5]1)([OH:3])=[O:2].[CH3:12]OC(OC)(C)C.S(=O)(=O)(O)O>CO>[C:1]([CH:4]1[CH2:11][C:7]2=[CH:8][O:9][CH:10]=[C:6]2[CH2:5]1)([O:3][CH3:12])=[O:2]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 64952,2-DimethoxypropaneHCID 158144045,6-Dihydro-4H-cyclopenta[c]furan-5-carboxylic acid

Product 1

HCID 158144055-(Carbomethoxy)-2,4,5,6-tetrahydrocyclopenta[c]furan

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve 5-(carboxy)-2,4,5,6-tetrahydro-cyclopenta[c]furan (3.6 g, 23.5 mmol) in methanol (60 mL) and treat with dimethoxypropane (5.8 mL, 47 mmol) and sulfuric acid (0.8 mL). Stir at room temperature for 1 day. Evaporate the solvent in vacuo, dilute with methylene chloride (75 mL) andwash with saturated sodium hydrogen carbonate (35 mL). Extract the aqueous phase with methylene chloride (30 mL), wash combined organics with brine (30 mL) and dry (Na2SO4). Evaporate the solvent in vacuo and pass through a plug of silica gel to give 5-(carbomethoxy)-2,4,5,6-tetrahydro-cyclopenta[c]furan.

Workup

  1. customEvaporate the solvent in vacuo
  2. additiondilute with methylene chloride (75 mL) andwash with saturated sodium hydrogen carbonate (35 mL)
  3. extractionExtract the aqueous phase with methylene chloride (30 mL)
  4. washwash
  5. dry with materialdry (Na2SO4)
  6. customEvaporate the solvent in vacuo and pass through a plug of silica gel

Sources & evidence

ORD record
ord-1ea79e70d8d948c98490ffb803032498
Source dataset
uspto-grants-1996_02
Patent number
US05491141

Reaction notes

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