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

HRID 375560Notes

Reaction equation

HRID 375560 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) and wash 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-tetrahydrocyclopenta[c]furan.

Workup

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

Sources & evidence

ORD record
ord-5d554696c7fc4588bd6f3a68b4d66092
Source dataset
uspto-grants-1996_01
Patent number
US05486513

Reaction notes

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