1-Propanol → 4-(4-Chlorophenylsulfonylmethyl)pyridine

HRID 2080355Notes

Reaction equation

C(O)CC.Cl.Cl[CH2:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([S:21]([O-:23])=[O:22])=[CH:17][CH:16]=1.[Na+].C([O-])(=O)C.[K+]>CCCCCC.C(OCC)(=O)C>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([S:21]([CH2:7][C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)(=[O:23])=[O:22])=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A 1-propanol (50 ml) solution of 4-chloromethylpyridine hydrochloride (1.26 g, 7.65 mmol), sodium 4-chlorobenzenesulfinate (1.52 g, 7.65 mmol) and potassium acetate (1.50 g, 15.3 mmol) was stirred under heating at 70° C. for 8 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The residue thus obtained was caused to pass through a short column (silica gel, ethyl acetate) and the eluate was concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography, and the fraction obtained from the hexane:ethyl acetate (=2:3) eluate was concentrated under reduced pressure to give the title compound (1.26 g, 62%) as a white solid.

Workup

temperatureThe reaction mixture was cooled to room temperature
concentrationconcentrated under reduced pressure
customThe residue thus obtained
concentrationthe eluate was concentrated under reduced pressure
customThe residue thus obtained
concentrationethyl acetate (=2:3) eluate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-a1ab7f0d38884e1c9d94335ac8848c7c
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932271B2

Reaction notes

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