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

HRID 1391675Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1391675
[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]

Komponenten

5

Edukt 4

HCID 6228DimethylformamideHCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 596760598-(Tert-butyl-dimethyl-silanyloxy)-6,11-dihydro-5-thia-11-aza-benzo[a]fluorene

Produkt 1

HCID 692860541-[8(tert-butyl-dimethyl-silanyloxy)-6H-5-thia-1-aza-benzo[a]fluoren-11-yl]-ethanone

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-8f6a1b0d41034bfcb501afb1b40df72c
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07338973B2

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