Tetrabutylammonium Fluoride → trans-7-nitro-5-(N-ethylsulfonyl-N-methylamino)-2,3,4,5-tetrahydro-1-benzoxepin-4-ol

HRID 2271072Notes

Reaction equation

HRID 2271072 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[O:19]1[CH:26]2[CH:20]1[CH2:21][CH2:22][O:23][C:24]1[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][C:25]=12.[CH3:34][N:35]([Si](C)(C)C)[S:36]([CH2:39][CH3:40])(=[O:38])=[O:37]>>[N+:31]([C:28]1[CH:29]=[CH:30][C:24]2[O:23][CH2:22][CH2:21][C@@H:20]([OH:19])[C@H:26]([N:35]([S:36]([CH2:39][CH3:40])(=[O:38])=[O:37])[CH3:34])[C:25]=2[CH:27]=1)([O-:33])=[O:32]

Participants

4

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 145805224,5-Epoxy-7-nitro-2,3,4,5-tetrahydro-benzoxepinHCID 15434534N-methyl-N-trimethylsilylethanesulfonamide

Product 1

HCID 15434531trans-7-nitro-5-(N-ethylsulfonyl-N-methylamino)-2,3,4,5-tetrahydro-1-benzoxepin-4-olYield 74.2%

Conditions

Temperature
65 °C

Procedure

2 g of tetrabutylammonium fluoride were added with stirring to a mixture of 6 g of 4,5-epoxy-7-nitro-2,3,4,5-tetrahydro-1-benzoxepine and 9.5 g of N-methyl-N-trimethylsilylethanesulfonamide. The reaction mixture was then heated for 3 h at 65° C., stirred overnight at RT and poured onto ammonium chloride solution. It was extracted several times with EA, and the organic phase was washed with water and dried over sodium sulfate. After concentration and recrystallization of the solid residue from isopropanol, 7.1 g of trans-7-nitro-5-(N-ethylsulfonyl-N-methylamino)-2,3,4,5-tetrahydro-1-benzoxepin-4-ol were obtained, m.p. 133-135° C.

Workup

  1. additionpoured onto ammonium chloride solution
  2. extractionIt was extracted several times with EA
  3. washthe organic phase was washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationAfter concentration and recrystallization of the solid residue from isopropanol

Sources & evidence

ORD record
ord-0eec2e3242694a3392fdda1c822a2421
Source dataset
uspto-grants-2001_12
Patent number
US06333349B1

Reaction notes

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