Sodium hydride → HCID 13149080, compound

HRID 1613608Notes

Reaction equation

HRID 1613608 reaction equation
[H-].[Na+].Br[C@H:4]1[C@H:10]([OH:11])[C:9]2[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=2[O:7][CH2:6][CH2:5]1>CS(C)=O>[O:11]1[CH:10]2[CH:4]1[CH2:5][CH2:6][O:7][C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=12

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 13149516HCID 13149516, compound

Product 1

HCID 13149080HCID 13149080, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

8.60 g (0.298 mole) of sodium hydride (80% dispersion in mineral oil) are introduced under argon into 320 ml of DMSO, and a solution of 243 g (0.259 mole) of trans-4-bromo-5-hydroxy-2,3,4,5-tetrahydro-1-benzoxepin in 180 ml of DMSO is added dropwise at room temperature within 2.5 hours. After 3 hours, the mixture is poured onto ice/water with stirring, and is extracted 3 times with diethyl ether. The combined organic phases are washed with water and saturated sodium chloride solution, dried over sodium sulfate and filtered, and the solvent is evaporated off in vacuo. The remaining 44 g of oil is distilled at 67°-69° C./0.01 torr.

Workup

  1. additionthe mixture is poured onto ice/water
  2. extractionis extracted 3 times with diethyl ether
  3. washThe combined organic phases are washed with water and saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent is evaporated off in vacuo
  7. distillationThe remaining 44 g of oil is distilled at 67°-69° C./0.01 torr

Sources & evidence

ORD record
ord-97c69892c95e4fec95e18d0f293978fb
Source dataset
uspto-grants-1993_03
Patent number
US05194442

Reaction notes

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