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

HRID 380159노트

반응식

HRID 380159 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-d41a473683704943a126fae0f8761451
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06300344B1

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