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

HRID 564316Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 564316
[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

Komponenten

7

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-5c840a32b7074569800b9335517e7f56
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067621B2

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