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

HRID 564316ノート

反応式

HRID 564316 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-5c840a32b7074569800b9335517e7f56
出典データセット
uspto-grants-2011_11
特許番号
US08067621B2

反応ノート

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