4-Toluenesulfonyl chloride → 5-(Benzyloxy)-2-(methoxycarbonyl)-3,4-dihydronaphthalene

HRID 1271267Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][CH:13]([C:20]([O:22][CH3:23])=[O:21])[CH:14]2O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1>N1C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][C:13]([C:20]([O:22][CH3:23])=[O:21])=[CH:14]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 5.96 g of 5-(benzyloxy)-1-hydroxy-2-(methoxycarbonyl)-1,2,3,4-tetrahydronaphthalene in 23 ml of anhydrous pyridine, 4.37 g of p-toluenesulfonyl chloride was added. After stirring with heating at 70° C. for 3 hours, 0.72 g of p-toluenesulfonyl chloride was further added, followed by stirring for 1.5 hours. The reaction solution was extracted with diethyl ether after adding iced water. The extract was washed in turn with water, 10% hydrochloric acid, water and an aqueous saturated sodium hydrogen carbonate solution and dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 2.79 g of the desired compound as a colorless crystal having a melting point of 64 to 67° C.

Workup

stirringby stirring for 1.5 hours
extractionThe reaction solution was extracted with diethyl ether
additionafter adding iced water
washThe extract was washed in turn with water, 10% hydrochloric acid, water
dry with materialan aqueous saturated sodium hydrogen carbonate solution and dried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-493c496a3d754fec87ce91a7b5292abd
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07205302B2

Reaction notes

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