Dichloromethane → 4-Chloro-phenylsulfanyl-5,8-difluoro-chroman-3-carbaldehyde
Reaction equation
ClC1C=CC(S[C@@H]2[C:18]3[C:13](=[C:14]([F:20])[CH:15]=[CH:16][C:17]=3[F:19])[O:12][CH2:11][C@H:10]2[CH2:21][OH:22])=CC=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)[C:33]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]1=2)=O.C(OCC)(=O)C.[S:51]([O-])([O-])(=O)=S.[Na+].[Na+].[CH2:58]([Cl:60])Cl>>[Cl:60][CH:58]1[C:18]2[C:13](=[C:14]([F:20])[CH:15]=[CH:16][C:17]=2[F:19])[O:12][CH:11]([S:51][C:33]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:10]1[CH:21]=[O:22]Participants
Procedure
Trans-[4-(4-chloro-phenylsulfanyl)-5,8-difluoro-chroman-3-yl]-methanol (Example 16 Step 2) (2.8 g, 8.8 mmole) was dissolved in 15 ml DCM and Dess-Martin reagent (4.1 g, 9.7 mmole) was then added. The reaction was stirred at room temperature for three hours. 40 ml EtOAc and 30 ml saturated sodium thiosulfate solution were added and the organic layer was washed with saturated sodium bicarbonate solution, dried over sodium sulfate and concentrated. The residue was used in next step without further purification.). Yield: 2.8 g, 100%. 1H NMR (CDCl3 400 MHz) δ 9.70 (s, 1H), 7.45 (d, J=8.8 Hz, 2H), 7.34 (d, J=8.8 Hz, 2H), 6.93-7.00 (m, 1H), 6.59-6.65 (m, 1H), 4.92 (dt, J=11.7 and 2.2 Hz, 1H), 4.89 (br, 1H), 4.74 (dd, J=11.7 and 2.9 Hz, 1H), 2.83 (m, 1H).
Workup
- washthe organic layer was washed with saturated sodium bicarbonate solution
- dry with materialdried over sodium sulfate
- concentrationconcentrated
- customThe residue was used in next step without further purification
Sources & evidence
- ORD record
- ord-645efeb219324509b9729b38a2aadcd3
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08569521B2
Reaction notes
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