Dichloromethane → 5-(3-chloropropyl)-2-methyl-5H-furo[3,2-c]pyridin-4-one

HRID 69051Notes

Reaction equation

HRID 69051 reaction equation
CS(Cl)(=O)=O.Cl[CH2:7][Cl:8].OC[CH2:11][CH2:12][N:13]1[CH:18]=[CH:17][C:16]2[O:19][C:20]([CH3:22])=[CH:21][C:15]=2[C:14]1=[O:23]>C(N(CC)CC)C>[Cl:8][CH2:7][CH2:11][CH2:12][N:13]1[CH:18]=[CH:17][C:16]2[O:19][C:20]([CH3:22])=[CH:21][C:15]=2[C:14]1=[O:23]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 669606955-(3-hydroxypropyl)-2-methyl-5H-furo[3,2-c]pyridine-4-one

Product 1

HCID 669605925-(3-chloropropyl)-2-methyl-5H-furo[3,2-c]pyridin-4-one

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Methane sulfonyl chloride (0.24 ml) was added to a dichloromethane solution (10 ml) of 5-(3-hydroxypropyl)-2-methyl-5H-furo[3,2-c]pyridine-4-one (0.28 g) and triethylamine (0.45 ml). The mixture was stirred at room temperature for two days. The reaction liquid was condensed under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4→1:1). The purified product was condensed to dryness under reduced pressure to give the title compound (0.16 g) as a white amorphous solid.

Workup

  1. customThe reaction liquid
  2. customcondensed under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4→1:1)
  4. customcondensed to dryness under reduced pressure

Sources & evidence

ORD record
ord-6c6bc373ac494d658fe4ad6ab8ca609c
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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