Methyl iodide → 3-(4-Chloro-benzenesulfonyl)-3-methyl-dihydrofuran-2-one

HRID 1924859Notes

Reaction equation

HRID 1924859 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]2[CH2:15][CH2:14][O:13][C:12]2=[O:16])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:20]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([C:11]2([CH3:20])[CH2:15][CH2:14][O:13][C:12]2=[O:16])(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 567327883-(4-Chlorobenzenesulfonyl)-dihydro-furan-2-one

Product 1

HCID 582805743-(4-Chloro-benzenesulfonyl)-3-methyl-dihydrofuran-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-(4-chlorobenzenesulfonyl)-dihydro-furan-2-one (0.599 g; 2.29 mmol) in DMF (5 mL) at 0-5° C. was added portionwise NaH (0.23 g of a 60% dispersion in mineral oil; 5.74 mmol). The mixture stirred 30 minutes and iodomethane (0.43 mL; 6.89 mmol) was added. The reaction warmed to room temperature while stiffing overnight and was quenched with water. The solid was filtered and dried in vacuo to provide the desired product. Wt 0.488 g. 1H NMR (CDCl3) δ 7.82 (d, 2H), 7.56 (d, 2H), 4.56 (m, 1H), 4.39 (m, 1H), 3.32 (m, 1H), 2.42 (m, 1H), 1.51 (s, 3H).

Workup

  1. waitwhile stiffing overnight
  2. customwas quenched with water
  3. filtrationThe solid was filtered
  4. customdried in vacuo

Sources & evidence

ORD record
ord-c6143190dc594a5cb2265798165d8af5
Source dataset
uspto-grants-2012_05
Patent number
US08178568B2

Reaction notes

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