Dimethylformamide → 1-[8(tert-butyl-dimethyl-silanyloxy)-6H-5-thia-1-aza-benzo[a]fluoren-11-yl]-ethanone
反応式
[C:1]([Si:5]([CH3:25])([CH3:24])[O:6][C:7]1[CH:8]=[C:9]2[C:17](=[CH:18][CH:19]=1)N[C:15]1[C:14]3[CH:20]=[CH:21][CH:22]=[CH:23][C:13]=3[S:12][CH2:11][C:10]2=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].C(Cl)(=[O:30])C.C[N:33]([CH:35]=O)[CH3:34]>>[C:1]([Si:5]([CH3:25])([CH3:24])[O:6][C:7]1[CH:8]=[C:9]2[C:17](=[CH:18][CH:19]=1)[CH:14]([C:20](=[O:30])[CH3:21])[C:15]1[C:34]3[N:33]=[CH:35][CH:22]=[CH:23][C:13]=3[S:12][CH2:11][C:10]2=1)([CH3:4])([CH3:3])[CH3:2]参加物
実験手順
8-(tert-Butyl-dimethyl-silanyloxy)-6,11-dihydro-5-thia-11-aza-benzo[a]fluorene (170 mg, 0.462 mmoL) in DMF (2 mL) was treated with NaH (60%, 37 mg, 0.925 mmoL) at 0° C. Acetyl chloride (52 mg, 0.693 mmoL) was added dropwise into the reaction 30 minutes later. The reaction mixture was than slowly warmed to room temperature over 2 hours. The reaction was quenched with saturated NH4Cl. The residue was partitioned between CH2Cl2 and saturated NaHCO3. The aqueous phase was extracted two times with CH2Cl2. The organic layer from each extraction was combined, washed with water, brine, dried over anhydrous Na2SO4, filtered and concentrated to yield a brown oil. The oil was then purified by column chromatography (silica gel, hexanes:EtOAc 5:1 as eluent) to yield the title compound as a pale solid.
後処理
- customThe reaction was quenched with saturated NH4Cl
- customThe residue was partitioned between CH2Cl2 and saturated NaHCO3
- extractionThe aqueous phase was extracted two times with CH2Cl2
- extractionThe organic layer from each extraction
- washwashed with water, brine
- dry with materialdried over anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customto yield a brown oil
- customThe oil was then purified by column chromatography (silica gel, hexanes:EtOAc 5:1 as eluent)
出典と根拠
- ORDレコード
- ord-8f6a1b0d41034bfcb501afb1b40df72c
- 出典データセット
- uspto-grants-2008_03
- 特許番号
- US07338973B2
反応ノート
読み込み中…