Sodium hydride → 1-[3-Chloro-4-(tetrahydro-pyran-4-ylsulfanyl)-phenyl]-ethanone

HRID 1098754Notes

Reaction equation

HRID 1098754 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[SH:8].[H-].[Na+].I[CH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[S:8][CH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27955064-iodotetrahydro-2H-pyranHCID 143653711-(3-Chloro-4-mercapto-phenyl)ethanone

Product 1

HCID 595061481-[3-Chloro-4-(tetrahydro-pyran-4-ylsulfanyl)-phenyl]-ethanoneYield 32%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product from step 1 (3.0 g, 16.07 mmol) was added to a suspension of sodium hydride (964.3 mg, 32.14 mmol) in DMF at 0° C. After 5 min 4-iodo-tetrahydro-pyran (3.41 g, 16.07 mmol) was added and the reaction mixture was stirred at RT for 1 h. The reaction mixture was quenched with water at 0° C. and neutralized with trifluoroacetic acid. Evaporation and purification of the crude product by silica gel chromatography using ethyl acetate/n-heptane gave the desired product (1.385 g, 32%)

Workup

  1. customThe reaction mixture was quenched with water at 0° C. and neutralized with trifluoroacetic acid
  2. customEvaporation and purification of the crude product by silica gel chromatography

Sources & evidence

ORD record
ord-4391c50ad48e4d599858a790c14d14c3
Source dataset
uspto-grants-2012_03
Patent number
US08143242B2

Reaction notes

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