Lawesson's reagent → 1-Mercapto-1,2,3,4-tetrahydro-5-methoxycarbonylmethoxynaphthalene

HRID 380159Notes

Reaction equation

HRID 380159 reaction equation
O[CH:2]1[C:11]2[C:6](=[C:7]([O:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH2:3]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:27])=CC=1>C1(C)C=CC=CC=1>[SH:27][CH:2]1[C:11]2[C:6](=[C:7]([O:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 183674011-Hydroxy-1,2,3,4-tetrahydro-5-methoxycarbonylmethoxynaphthalene

Product 1

HCID 183673561-Mercapto-1,2,3,4-tetrahydro-5-methoxycarbonylmethoxynaphthaleneYield 104.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1-hydroxy-1,2,3,4-tetrahydro-5-methoxycarbonylmethoxynaphthalene (0.42 g) and Lawesson's reagent (0.40 g) in toluene (4 ml) was refluxed under N2 atmosphere for 1 hour. The reaction mixture was purified by chromatography on silica gel to give 1-mercapto-1,2,3,4-tetrahydro-5-methoxycarbonylmethoxynaphthalene (0.26 g). A solution of 1-mercapto-1,2,3,4-tetrahydro-5-methoxycarbonylmethoxynaphthalene (0.26 g), (4,5-diphenyloxazol-2-yl)methyl bromide (0.32 g) and potassium carbonate (0.14 g) in DMF (5 ml) was stirred for 6 hours at room temperature. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine. The dried solvent was evaporated in vacuo. The residue was purified by chromatography on silica gel to give 1-[(4,5-diphenyloxazol-2-yl)methylthio]-1,2,3,4-tetrahydro-5-methoxycarbonylmethoxynaphthalene (0.29 g).

Workup

  1. customThe reaction mixture was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-d41a473683704943a126fae0f8761451
Source dataset
uspto-grants-2001_10
Patent number
US06300344B1

Reaction notes

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