Hydrochloric Acid → HCID 20150393, compound

HRID 568730Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:9]([CH2:12][CH2:13][OH:14])([CH3:11])[CH2:8][CH2:7][C:6]=2[CH:15]=1.[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1.Cl>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:9]([CH3:11])([CH2:12][CH2:13][O:14][S:22]([C:19]3[CH:20]=[CH:21][C:16]([CH3:26])=[CH:17][CH:18]=3)(=[O:24])=[O:23])[CH2:8][CH2:7][C:6]=2[CH:15]=1

Participants

Conditions

Temperature: 0 °C

Procedure

In a nitrogen atmosphere, 11.0 g (0.0495 mol) of 6-chloro-3,4-dihydro-2-(2-hydroxyethyl)-2-methyl-2H-benzopyran was dissolved in 50 ml of pyridine, the solution was cooled to 0° C. and, with vigorous stirring, 11.3 g of p-toluenesulfonyl chloride was added gradually thereto. After stirring at 0° C. for 1 hour, the reaction mixture was poured into 300 ml of dilute hydrochloric acid and extracted with diethyl ether. The ether layer was washed with water, dried over anhydrous magnesium sulfate and filtered. Low-boiling substances were distilled off from the filtrate under reduced pressure, and the residue was purified by silica gel column chromatography to give 15.3 g of 6-chloro-3,4-dihydro-2-methyl-2-[2-(p-toluenesulfonyloxy)ethyl]-2H-benzopyran.

Workup

additionwas added gradually
extractionextracted with diethyl ether
washThe ether layer was washed with water
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
distillationLow-boiling substances were distilled off from the filtrate under reduced pressure
customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-9a94aa35358b4aed983d42ca279a7d6e
Source dataset: uspto-grants-1988_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04728650

Reaction notes

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