Sodium hydride → 2-(Methylsulfonyl)-2,3-dihydropyrano[3,2-e]isoindol-1(7h)-one

HRID 1727404Notes

Reaction equation

HRID 1727404 reaction equation
[C:1]1(=[O:14])[C:9]2[C:8]3[CH:10]=[CH:11][CH2:12][O:13][C:7]=3[CH:6]=[CH:5][C:4]=2[CH2:3][NH:2]1.[H-].[Na+].[CH3:17][S:18](Cl)(=[O:20])=[O:19]>C1COCC1>[CH3:17][S:18]([N:2]1[C:1](=[O:14])[C:9]2[C:8]3[CH:10]=[CH:11][CH2:12][O:13][C:7]=3[CH:6]=[CH:5][C:4]=2[CH2:3]1)(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 575676832,3-dihydropyrano[3,2-e]isoindol-1(7H)-one

Product 1

HCID 575676842-(Methylsulfonyl)-2,3-dihydropyrano[3,2-e]isoindol-1(7h)-oneYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,3-dihydropyrano[3,2-e]isoindol-1(7H)-one (71) (500 mg, 2.67 mmol) in THF (35 ml) was added NaH (95%, 87 mg, 3.47 mmol) in portions. Resulting mixture was stirred for 40 min before adding MeSO2Cl by syringe. Stirring was continued for 1 hour. The solvent was removed in vacuo and the residue was portioned with CH2Cl2. The organic solution was washed with H2O, sat. NaCl and dried over Na2SO4. Concentration in vacuo gave the title compound (95) as a solid (490 mg, 69%). MS (ES) m/z 266.0.

Workup

  1. customResulting mixture
  2. stirringStirring
  3. waitwas continued for 1 hour
  4. customThe solvent was removed in vacuo
  5. washThe organic solution was washed with H2O, sat. NaCl
  6. dry with materialdried over Na2SO4
  7. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-7748191cd1b54456aaab4873d3bfad8c
Source dataset
uspto-grants-2009_02
Patent number
US07495111B2

Reaction notes

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