Sodium → 4,5-Epoxy-7-nitro-2,3,4,5-tetrahydro-benzoxepin

HRID 1613612Notes

Reaction equation

HRID 1613612 reaction equation
[Na].Br[C@H:3]1[C@H:9]([OH:10])[C:8]2[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:7]=2[O:6][CH2:5][CH2:4]1>CO>[O:10]1[CH:9]2[CH:3]1[CH2:4][CH2:5][O:6][C:7]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:8]=12

Participants

4

Reactant 2

HCID 5360545SodiumHCID 67883955trans-4-Bromo-5-hydroxy-7-nitro-2,3,4,5-tetrahydro-1-benzoxepin

Product 1

HCID 145805224,5-Epoxy-7-nitro-2,3,4,5-tetrahydro-benzoxepin

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

2.65 g (0.115 mole) of metallic sodium are dissolved in 220 ml of methanol and, while stirring, a solution of 31.7 g (0.11 mole) of trans-4-bromo-5-hydroxy-7-nitro-2,3,4,5-tetrahydro-1-benzoxepin in 230 ml of methanol is added dropwise at room temperature. After 2.5 hours the precipitated solid is filtered off with suction and washed with methanol, and the filtrate is evaporated in vacuo. The residue is a solid of melting point 121°-123° C.

Workup

  1. filtrationAfter 2.5 hours the precipitated solid is filtered off with suction
  2. washwashed with methanol
  3. customthe filtrate is evaporated in vacuo

Sources & evidence

ORD record
ord-6ee30e63b98f4bc0b1c9ec5b7a5d09bb
Source dataset
uspto-grants-1993_03
Patent number
US05194442

Reaction notes

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