Sodium hydride → HCID 18448189, compound

HRID 1268992Notes

Reaction equation

HRID 1268992 reaction equation
[OH:1][C:2]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[H-].[Na+].[CH2:15]([O:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1)[C:16]#[C:17][CH3:18]>O1CCCC1>[CH2:15]([O:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([O:1][C:2]2[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:3]=2[C:4]([O:6][CH3:7])=[O:5])(=[O:28])=[O:27])=[CH:22][CH:21]=1)[C:16]#[C:17][CH3:18]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 31835Benzoic acid, 2-hydroxy-3-methyl-, methyl esterHCID 111959284-But-2-ynyloxy-benzenesulfonyl chloride

Product 1

HCID 18448189HCID 18448189, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.50 g (3.012 mmol) of methyl 2-hydroxy-3-methyl-benzoate in 20 mL of tetrahydrofuran (THF) is added 0.133 g (3.313 mmol) of a 60% oil dispersion of sodium hydride. The reaction mixture is stirred for 1 h at room temperature and then 0.739 g (3.012 mmol) of 4-but-2-ynyloxy benzenesulfonyl chloride is added. The resulting mixture is stirred at room temperature for 15 h and then quenched with saturated ammonium chloride solution. The resulting mixture is extracted with ether and the combined organics are then washed with water and brine. The organic layer is then dried over MgSO4, filtered and concentrated in vacuo. The residue is chromatographed on silica gel eluting with ethyl acetate/hexanes (1:3) to provide 0.93 g (83%) of methyl 2-({[4-(2-butynyloxy)phenyl]sulfonyl}oxy)-3-methylbenzoate as a white solid. Electrospray Mass Spec: 374.8 (M+H)+

Workup

  1. stirringThe resulting mixture is stirred at room temperature for 15 h
  2. customquenched with saturated ammonium chloride solution
  3. extractionThe resulting mixture is extracted with ether
  4. washthe combined organics are then washed with water and brine
  5. dry with materialThe organic layer is then dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue is chromatographed on silica gel eluting with ethyl acetate/hexanes (1:3)

Sources & evidence

ORD record
ord-6d9a5b66100447f6981edccf0828bc2a
Source dataset
uspto-grants-2007_04
Patent number
US07199155B2

Reaction notes

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