Potassium Carbonate → 1-[(4,5-Diphenyloxazol-2-yl)methylthio]-1,2,3,4-tetrahydro-5-methoxycarbonylmethoxynaphthalene

HRID 1741425노트

반응식

HRID 1741425 반응식
[SH:1][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.[C:18]1([C:24]2[N:25]=[C:26]([CH2:35]Br)[O:27][C:28]=2[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:18]1([C:24]2[N:25]=[C:26]([CH2:35][S:1][CH:2]3[C:11]4[C:6](=[C:7]([O:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH:8]=[CH:9][CH:10]=4)[CH2:5][CH2:4][CH2:3]3)[O:27][C:28]=2[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 5685992-Bromomethyl-4,5-diphenyl-oxazoleHCID 183673561-Mercapto-1,2,3,4-tetrahydro-5-methoxycarbonylmethoxynaphthalene

생성물 1

HCID 183674061-[(4,5-Diphenyloxazol-2-yl)methylthio]-1,2,3,4-tetrahydro-5-methoxycarbonylmethoxynaphthalene수율 58.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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 (0.20 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). MS (m/z): 486 (M+ +1) NMR (CDCl3, δ): 1.75-1.92 (1H, m), 2.00-2.22 (3H, m), 2.45-2.72 (1H, m), 2.80-3.02 (1H, m), 3.79 (3H, s), 3.91 (1H, s), 3.94 (1H, s), 4.36 (1H, m), 4.60 (2H, s), 6.50-6.55 (1H, m), 7.04-7.06 (2H, m), 7.33-7.40 (6H, m), 7.59-7.68 (4H, m)

후처리

  1. customThe mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. customThe dried solvent was evaporated in vacuo
  4. customThe residue was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-480c2febef7a45b68a06362e27a47f36
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05972965

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