Boron trifluoride etherate → HCID 13988265, compound

HRID 1275691Notes

Reaction equation

HRID 1275691 reaction equation
[OH:1][CH:2]1[C@@H:7]2[C:8]([CH2:11][OH:12])=[CH:9][CH2:10][C@@H:6]2[C:5]([C:13]([O:15][CH3:16])=[O:14])=[CH:4][O:3]1.FB(F)F.[CH2:21](OCC)C.C(=O)(O)[O-].[Na+].CCCCCC.C(OC(=O)C)C>CO>[OH:12][CH2:11][C:8]1[C@H:7]2[C@H:2]([O:1][CH3:21])[O:3][CH:4]=[C:5]([C:13]([O:15][CH3:16])=[O:14])[C@H:6]2[CH2:10][CH:9]=1

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 516892Sodium BicarbonateHCID 6325197HCID 6325197, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 13988265HCID 13988265, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5 g (22.1 mmol) of methyl (4aS,7aS)-1-hydroxy-7-hydroxymethyl-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate was dissolved in 25 ml of methanol and catalytic amount of trifluoroboron diethylether was added thereto. The reaction mixture was stirred at room temperature for 20 hours and then the reaction was stopped by the addition of saturated aqueous sodium bicarbonate solution. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and distilled under vacuum. The residue was purified by silica gel column chromatography (eluent: n-hexane/ethylacetate=5/1, v/v) to obtain 5.26 g (Yield 100%) of methyl (1R,4aS,7aS)-7-hydroxymethyl-1-methoxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate as an oil.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. distillationdistilled under vacuum
  5. customThe residue was purified by silica gel column chromatography (eluent

Sources & evidence

ORD record
ord-9b8a2d5e931948fabb0506aa65147772
Source dataset
uspto-grants-2000_12
Patent number
US06162826

Reaction notes

Loading…