Water → HCID 117778975, compound

HRID 2206543Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][C:4]([CH:7]([OH:9])[CH3:8])=[CH:3][CH:2]=1.[H-].[Na+].[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.O>C1COCC1>[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([O:9][CH:7]([C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)[CH3:8])(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1-(pyridine-4-yl)ethanol (400 mg, 3.25 mmol) in THF (10 mL) was added sodium hydride (301 mg, 12.54 mmol) at 0° C. The mixture was stirred at 0° C. for 30 min. 4-methylbenzene-1-sulfonyl chloride (744 mg, 3.90 mmol) was added and the mixture was stirred at room temperature for 4 hr. Water (10 mL) was added and THF was removed under reduced pressure. The residue was extracted with ethyl acetate (20 mL×3). The organic layer was washed with brine and dried over sodium sulfate. The solvent was removed under vacuum and the residue was purified by column chromatography on silica gel (eluted: petroleum ether/ethyl acetate=2/1) to give 1-(pyridine-4-yl)ethyl 4-methylbenzenesulfonate (0.56 g, 62.2%). LCMS 278 (M+H+).

Workup

stirringthe mixture was stirred at room temperature for 4 hr
customTHF was removed under reduced pressure
extractionThe residue was extracted with ethyl acetate (20 mL×3)
washThe organic layer was washed with brine
dry with materialdried over sodium sulfate
customThe solvent was removed under vacuum
customthe residue was purified by column chromatography on silica gel (eluted: petroleum ether/ethyl acetate=2/1)

Sources & evidence

ORD record: ord-a166bc0ec1c14608864d11327f20b940
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371331B2

Reaction notes

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