Pyridine, 2-[(trimethylsilyl)oxy]- → HCID 67884043, compound

HRID 1613602Notes

Reaction equation

HRID 1613602 reaction equation
[OH2:1].O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Br[C@H:23]1[C@H:29](O)[C:28]2[CH:31]=[C:32]([S:35]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[O:36])[CH:33]=[CH:34][C:27]=2[O:26][CH2:25][CH2:24]1.C[Si](C)(C)[O:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][N:47]=1>>[O:45]=[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][N:47]1[C@@H:29]1[C:28]2[CH:31]=[C:32]([S:35]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[O:36])[CH:33]=[CH:34][C:27]=2[O:26][CH2:25][CH2:24][C@H:23]1[OH:1]

Participants

4

Reactant 3

HCID 10975862Pyridine, 2-[(trimethylsilyl)oxy]-HCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 67883795trans-4-Bromo-5-hydroxy-7-phenylsulfinyl-2,3,4,5-tetrahydro-1-benzoxepin

Product 1

HCID 67884043HCID 67884043, compound

Conditions

Temperature
60 °C

Procedure

8.60 g (27.3 mmol) of tetrabutylammonium fluoride trihydrate are added to a mixture of 4.00 g (10.9 mmol) of trans-4-bromo-5-hydroxy-7-phenylsulfinyl-2,3,4,5-tetrahydro-1-benzoxepin and 6.40 g (38.3 mmol) of 2-trimethylsilyloxypyridine, and a mixture is subsequently stirred at 60° C. for 5 hours. The cooled syrupy liquid is poured onto ice-water and extracted several times with ethyl acetate. The combined ethyl acetate extracts are washed with water and saturated sodium chloride solution, dried over sodium sulfate, filtered and evaporated. The foamy residue is crystallized in butyl acetate. White crystals of melting point 181°-184° C. are obtained.

Workup

  1. additionThe cooled syrupy liquid is poured onto ice-water
  2. extractionextracted several times with ethyl acetate
  3. washThe combined ethyl acetate extracts are washed with water and saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe foamy residue is crystallized in butyl acetate
  8. customWhite crystals of melting point 181°-184° C. are obtained

Sources & evidence

ORD record
ord-37455526beb64936be4509d373808791
Source dataset
uspto-grants-1993_03
Patent number
US05194442

Reaction notes

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