Benzyl Alcohol → HCID 53761132, compound

HRID 1275697Notes

Reaction equation

HRID 1275697 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.[CH2:17](O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.FB(F)F.C(OCC)C>O1CCCC1>[CH2:17]([O:1][C@H: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)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 8000Boron trifluoride etherateHCID 6325197HCID 6325197, compound

Product 1

HCID 53761132HCID 53761132, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

1.13 g (5.0 mmol) of methyl (4aS,7aS)-1-hydroxy-7-hydroxymethyl-1,4a,5, 7a-tetrahydrocyclopenta[c]pyran-4-carboxylate was dissoved in 10 ml of dried tetrahydrofuran, then 2.60 ml (25 mmol) of benzyl alcohol and catalytic amount of trifluoroboron diethylether were added thereto. The resulting mixture was stirred while refluxing for 48 hours at 75° C. The mixture was cooled down to room temperature and concentrated. The residue was dissolved in ethylacetate and then washed with saturated aqueous sodium bicarbonate solution and saturated saline solution The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by silica gel column chromatography (eluent: n-hexanelethylacetate=2/1, v/v) to obtain 0.61 g (Yield 39%) of methyl (1R,4aS,7aS)-1-benzyloxy-7-hydroxymethyl-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate as an oil.

Workup

  1. temperatureThe mixture was cooled down to room temperature
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in ethylacetate
  4. washwashed with saturated aqueous sodium bicarbonate solution and saturated saline solution The organic layer
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography (eluent

Sources & evidence

ORD record
ord-f0529fe3c67a43cc97342aadde782d08
Source dataset
uspto-grants-2000_12
Patent number
US06162826

Reaction notes

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