Potassium Carbonate → Methyl 4-tetrahydrofuran-3-ylsulfanylbenzoate

HRID 713063노트

반응식

HRID 713063 반응식
[SH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].I[CH:19]1[CH2:23][CH2:22][O:21][CH2:20]1>CN(C=O)C.C(Cl)Cl>[O:21]1[CH2:22][CH2:23][CH:19]([S:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=2)[CH2:20]1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 237573Methyl 4-sulfanylbenzoateHCID 221392643-Iodotetrahydrofuran

생성물 1

HCID 68290908Methyl 4-tetrahydrofuran-3-ylsulfanylbenzoate수율 86%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

To a suspension of methyl 4-sulfanylbenzoate (0.85 g, 5.05 mmol), potassium carbonate (1.39 g, 10.1 mmol) in DMF (10 mL) at room temperature was added 3-iodotetrahydrofuran (1.00 g, 5.05 mmol). The resulting suspension was stirred for 16 hours. The reaction mixture was diluted with DCM (25 mL), filtered and the solvent was evaporated under reduced pressure. The residue was dissolved in DCM (25 mL) and washed with water (3×15 mL) and saturated aqueous brine solution (1×15 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to yield methyl 4-tetrahydrofuran-3-ylsulfanylbenzoate (1.03 g, 86%) as a yellow solid. ESI-MS m/z calc. 238.1. found 239.3 (M+1)+; Retention time: 1.47 minutes (3 min run); 1H NMR (400 MHz, DMSO) δ 7.91-7.83 (m, 2H), 7.48-7.39 (m, 2H), 4.16-4.08 (m, 2H), 3.91-3.72 (m, 5H), 3.55 (q, J=7.6 Hz, 1H), 2.49-2.35 (m, 1H), 1.86-1.74 (m, 1H).

후처리

  1. filtrationfiltered
  2. customthe solvent was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in DCM (25 mL)
  4. washwashed with water (3×15 mL) and saturated aqueous brine solution (1×15 mL)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-5d16070897154b24a7c9636bc6b1c115
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181273B2

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