Sodium Thiosulfate → 3-(2-Benzyloxy-ethoxymethyl)-4-(4-chloro-benzenesulfonyl)-5,8-difluoro-chroman

HRID 564316노트

반응식

HRID 564316 반응식
[CH2:1]([O:8][CH2:9][CH2:10][O:11][CH2:12][CH:13]1[CH:22](SC2C=CC(Cl)=CC=2)[C:21]2[C:16](=[C:17]([F:32])[CH:18]=[CH:19][C:20]=2[F:31])[O:15][CH2:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:33]1[CH:38]=[C:37]([Cl:39])[CH:36]=[C:35](C(OO)=O)[CH:34]=1.[S:44]([O-:48])([O-])(=[O:46])=S.[Na+].[Na+]>C(Cl)Cl.O.C(OCC)(=O)C>[CH2:1]([O:8][CH2:9][CH2:10][O:11][CH2:12][CH:13]1[CH:22]([S:44]([C:34]2[CH:33]=[CH:38][C:37]([Cl:39])=[CH:36][CH:35]=2)(=[O:48])=[O:46])[C:21]2[C:16](=[C:17]([F:32])[CH:18]=[CH:19][C:20]=2[F:31])[O:15][CH2:14]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 670064253-(2-Benzyloxy-ethoxymethyl)-4-(4-chloro-phenylsulfanyl)-5,8-difluoro-chroman

생성물 1

HCID 670069033-(2-Benzyloxy-ethoxymethyl)-4-(4-chloro-benzenesulfonyl)-5,8-difluoro-chroman

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

3-(2-Benzyloxy-ethoxymethyl)-4-(4-chloro-phenylsulfanyl)-5,8-difluoro-chroman (0.42 g, 0.88 mmole) was dissolved in 15 ml DCM and MCPBA (77%, 0.6 g, 2.6 mmole) was added. The reaction was stirred at room temperature for 30 minutes. 0.5 g sodium thiosulfate in 50 ml water and 50 ml EtOAc were added. The organic layer washed with 1N NaOH solution (50 ml), brine (50 ml), dried over sodium sulfate and concentrated. The product was purified by column (EtOAc/hexane from 0/100 to 50/50 in 45 minutes). Yield: 0.40 g, 89%. 1H NMR (CDCl3 400 MHz δ 7.73 (d, J=8.8 Hz, 2H), 7.4 (d, J=8.1 Hz, 2H), 7.25-7.37 (m, 5H), 7.02 (m, 1H), 6.42 (m, 1H), 4.90 (dd, J=11.7 and 2.9 Hz, 1H), 4.63 (s, 1H), 4.50 (s, 2H), 4.38 (t, J=11.0, 1H), 3.45-3.62 (m, 5H), 3.30 (t, J=9.5 Hz, 1H), 3.13 (m, 1H).

후처리

  1. washThe organic layer washed with 1N NaOH solution (50 ml), brine (50 ml)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customThe product was purified by column (EtOAc/hexane from 0/100 to 50/50 in 45 minutes)

출처 및 근거

ORD 기록
ord-5c840a32b7074569800b9335517e7f56
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08067621B2

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