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

HRID 1072203Notes

Reaction equation

HRID 1072203 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-ae60ae53eba2432d97a6640b3fdd5a37
Source dataset
uspto-grants-2005_06
Patent number
US06908947B2

Reaction notes

Loading…