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Acetyl chloride → 1-[8(tert-butyl-dimethyl-silanyloxy)-6H-5-thia-11-aza-benzo[a]fluoren-11-yl]-ethanone

HRID 624488
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HRID 624488 반응식
[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)[NH:16][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:28](Cl)(=[O:30])[CH3:29]>CN(C=O)C>[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:16]([C:28](=[O:30])[CH3:29])[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 596760598-(Tert-butyl-dimethyl-silanyloxy)-6,11-dihydro-5-thia-11-aza-benzo[a]fluorene

생성물 1

HCID 596760521-[8(tert-butyl-dimethyl-silanyloxy)-6H-5-thia-11-aza-benzo[a]fluoren-11-yl]-ethanone

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  1. customThe reaction was quenched with saturated NH4Cl
  2. customThe residue was partitioned between CH2Cl2 and saturated NaHCO3
  3. extractionThe aqueous phase was extracted two times with CH2Cl2
  4. extractionThe organic layer from each extraction
  5. washwashed with water, brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto yield a brown oil
  10. customThe oil was then purified by column chromatography (silica gel, hexanes:EtOAc 5:1 as eluent)

출처 및 근거

ORD 기록
ord-ba4b82d11b6040cc9d6f515d365e0ed0
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09303037B2

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