Water → HCID 9909128, compound

HRID 1656452Notes

Reaction equation

HRID 1656452 reaction equation
C[Si](C)(C)[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.[O:12]1[CH:18]2[CH:13]1[C:14]([CH3:31])([CH3:30])[O:15][C:16]1[CH:22]=[CH:21][C:20]([S:23]([C:26]([F:29])([F:28])[F:27])(=[O:25])=[O:24])=[CH:19][C:17]=12.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[O:3]=[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]1[C@@H:18]1[C:17]2[CH:19]=[C:20]([S:23]([C:26]([F:27])([F:29])[F:28])(=[O:25])=[O:24])[CH:21]=[CH:22][C:16]=2[O:15][C:14]([CH3:30])([CH3:31])[C@H:13]1[OH:12]

Participants

6

Reactant 4

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 10975862Pyridine, 2-[(trimethylsilyl)oxy]-HCID 15036013HCID 15036013, compound

Product 1

HCID 9909128HCID 9909128, compoundYield 38.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.63 g of 2-trimethylsilyloxypyridine was added to a solution of 1.00 g of 3,4-epoxy-3,4-dihydro-2,2-dimethyl-6-trifluoromethylsulfonyl-2H-1-benzopyran (prepared as described in Preparation 8) in 1.2 ml of anhydrous tetrahydrofuran, and a solution of 2.54 g of tetrabutylammonium fluoride in anhydrous tetrahydrofuran was added to the resulting mixture through a syringe, whilst ice-cooling and under an atmosphere of nitrogen. The reaction mixture was stirred at room temperature for 72 hours, after which it was poured into water and extracted with ethyl acetate. The extract was then washed with water, with a 5% w/v aqueous solution of hydrochloric acid, with an aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, after which it was dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 2:1 by volume mixture of ethyl acetate and cyclohexane as the eluent, to afford 503 mg of the title compound as about a 1:1 mixture of rotational isomers, melting at 219°-220° C.

Workup

  1. temperaturecooling and under an atmosphere of nitrogen
  2. extractionextracted with ethyl acetate
  3. washThe extract was then washed with water, with a 5% w/v aqueous solution of hydrochloric acid, with an aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride
  4. dry with materialafter which it was dried over anhydrous magnesium sulfate
  5. customThe solvent was then removed by distillation under reduced pressure
  6. customThe resulting residue was purified by column chromatography through silica gel
  7. additionby volume mixture of ethyl acetate and cyclohexane as the eluent

Sources & evidence

ORD record
ord-bb9b7976316b40b9ba7e327540021dd8
Source dataset
uspto-grants-1993_10
Patent number
US05254578

Reaction notes

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