Sodium hydride → 2,3,4,5-Tetrahydro-1-benzoxepine

HRID 1722640Notes

Reaction equation

HRID 1722640 reaction equation
[H-].[Na+].S(O[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[OH:20])(C1C=CC(C)=CC=1)(=O)=O>C1COCC1.C(OCC)(=O)C.[Cl-].[Na+].O.O>[O:20]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[CH2:16][CH2:15][CH2:14][CH2:19]1

Participants

7

Reactant 2

HCID 24758Sodium hydrideHCID 17221462-Hydroxyphenyl 4-methylbenzenesulfonate

Product 1

HCID 225522,3,4,5-Tetrahydro-1-benzoxepine

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a mixture of 18.22 g of sodium hydride (60% dispersed in mineral oil) and 200 ml THF is added dropwise at 0° C. a solution of 146 g of o-tosyloxyphenol in 100 ml of THF. The reaction mixture is allowed to come to room temperature overnight. The reaction mixture is then chilled and 20 ml of H2O is added slowly. The mixture is then diluted with ethyl acetate and with brine and water. The organic layer is dried (MgSO4), filtered, and concentrated purification by flash column chromatography affords 2,3,4,5-tetrahydro-1-benzoxepin.

Workup

  1. temperatureThe reaction mixture is then chilled
  2. dry with materialThe organic layer is dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurification by flash column chromatography

Sources & evidence

ORD record
ord-5253511bb2b148de804bea3c85ae8470
Source dataset
uspto-grants-1989_08
Patent number
US04857517

Reaction notes

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