Potassium Carbonate → (3R,3aS,6aR)-hexahydrofuro(2,3-b)furan-3-ol

Reaction equation

C([O:4][C@@H:5]1[C@H:12]2[C@H:8]([O:9][CH2:10][CH2:11]2)[O:7][CH2:6]1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>ClCCl.CO>[O:7]1[C@H:8]2[O:9][CH2:10][CH2:11][C@H:12]2[C@@H:5]([OH:4])[CH2:6]1

Participants

Conditions

Temperature: 30 °C

Procedure

(3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-yl acetate (8.0 g) was dissolved in dichloromethane (24 ml) and Methanol (24 ml). Potassium carbonate (0.1 g) was added and reaction mass was stirred at 25-35° C. till the completion of reaction. Reaction mass was filtered & concentrated under vacuum at 40-45° C. to residue of (3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-ol (Yield 6.5 g).

Workup

customreaction mass
customReaction mass
filtrationwas filtered
concentrationconcentrated under vacuum at 40-45° C. to residue of (3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-ol (Yield 6.5 g)

Sources & evidence

ORD record: ord-7fb413531e564110ada8de0058b82c76
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841467B2

Reaction notes

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Participants

Reactant 2

HCID 11430Potassium Carbonate

HCID 59959307(3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-yl acetate

Product 1

HCID 9942150(3R,3aS,6aR)-hexahydrofuro(2,3-b)furan-3-ol

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent

HCID 6344DichloromethaneSolvent