Boron trifluoride etherate → HCID 46177287, compound

HRID 1384996Notes

Reaction equation

HRID 1384996 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C@H:10]2[CH2:11][CH:12]=[C:13]([CH2:14][OH:15])[C@H:9]2[C@H:8]([OH:16])[O:7][CH:6]=1)=[O:4].FB(F)F.[CH2:21](OCC)C.C(=O)(O)[O-].[Na+]>CO>[OH:15][CH2:14][C:13]1[C@@H:9]2[C@@H:10]([C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][O:7][CH:8]2[O:16][CH3:21])[CH2:11][CH:12]=1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 442424GenipinHCID 516892Sodium Bicarbonate

Product 1

HCID 46177287HCID 46177287, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Genipin (5 g, 22.1 mmol) was dissolved with 250 ml of methanol and catalytic amount of trifluoroboron diethylether was added, and stirred for 3 hours, then saturated sodium bicarbonate solution was added to finish the reaction. Under reduce pressure, methanol was removed and extracted with ethylacetate, and dried, filtered and concentrated with anhydous magnesium sulfate. Oily phase of methyl (3aS,7aS)-1-hydroxymethyl-7-methoxy-3,7,3a,7a-tetrahydro-6-oxaindene-4-carboxylate (5.26 g, 7S:7R=1:3) was obtained.

Workup

  1. additionwas added
  2. customthe reaction
  3. customwas removed
  4. extractionextracted with ethylacetate
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated with anhydous magnesium sulfate

Sources & evidence

ORD record
ord-63c8d32ac56947a6960d2d9a0b109ec6
Source dataset
uspto-grants-2001_07
Patent number
US06262083B1

Reaction notes

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