Borane → [4-Chloro-3-(1,1-dioxo-1lambda6-thiomorpholin-4-yl)-5-ethoxy-phenyl]-methanol
Reaktionsgleichung
[Cl:1][C:2]1[C:10]([O:11][CH2:12][CH3:13])=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[N:14]1[CH2:19][CH2:18][S:17](=[O:21])(=[O:20])[CH2:16][CH2:15]1.B>>[Cl:1][C:2]1[C:10]([O:11][CH2:12][CH3:13])=[CH:9][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[N:14]1[CH2:15][CH2:16][S:17](=[O:21])(=[O:20])[CH2:18][CH2:19]1Komponenten
Versuchsvorschrift
To a solution of 4-chloro-3-(1,1-dioxo-1λ6-thiomorpholin-4-yl)-5-ethoxy-benzoic acid (0.17 g, 0.51 mmol, 1.0 equiv) was added borane (1.02 mL, 1.02 mmol, 2.0 equiv; 1 M solution in THF) and the reaction mixture stirred at rt overnight. The reaction was quenched by addition of a few drops of methanol, ethyl acetate was added (50 mL) and the organic phase washed with a 1 M solution of NaOH (3×20 mL). The organic phase was dried over MgSO4, the solvent removed by evaporation under reduced pressure and the crude material used in the next step without further purification. Yield: 0.089 g (58%). 1H NMR (300 MHz, CDCl3): δ 1.39 (t, J=7.0 Hz, 3H), 3.13-3.16 (m, 4H), 3.42-3.45 (m, 4H), 4.04 (q, J=7.0 Hz, 2H), 4.56 (s, 2H), 6.64 (br s, 1H), 6.67 (br s, 1H).
Aufarbeitung
- customThe reaction was quenched by addition of a few drops of methanol, ethyl acetate
- additionwas added (50 mL)
- washthe organic phase washed with a 1 M solution of NaOH (3×20 mL)
- dry with materialThe organic phase was dried over MgSO4
- customthe solvent removed by evaporation under reduced pressure
- customthe crude material used in the next step without further purification
Quellen und Nachweise
- ORD-Eintrag
- ord-3a1d46ce7c49490da316f8b886fb5117
- Quelldatensatz
- uspto-grants-2010_01
- Patentnummer
- US07645753B2
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