Tetrabutylammonium Fluoride → 1-(8-hydroxythiochromeno[4,3-b]indol-11(6H)-yl)ethanone

HRID 1880463Notes

Reaction equation

HRID 1880463 reaction equation
C([Si](C)(C)[O:6][C:7]1[CH:8]=[C:9]2[C:17](=[CH:18][CH:19]=1)[N:16]([C:20](=[O:22])[CH3:21])[C:15]1[C:14]3[CH:23]=[CH:24][CH:25]=[CH:26][C:13]=3[S:12][CH2:11][C:10]2=1)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:6][C:7]1[CH:8]=[C:9]2[C:17](=[CH:18][CH:19]=1)[N:16]([C:20](=[O:22])[CH3:21])[C:15]1[C:14]3[CH:23]=[CH:24][CH:25]=[CH:26][C:13]=3[S:12][CH2:11][C:10]2=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 596760521-[8(tert-butyl-dimethyl-silanyloxy)-6H-5-thia-11-aza-benzo[a]fluoren-11-yl]-ethanone

Product 1

HCID 444118781-(8-hydroxythiochromeno[4,3-b]indol-11(6H)-yl)ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-[8(tert-butyl-dimethyl-silanyloxy)-6H-5-thia-11-aza-benzo[a]fluoren-11-yl]-ethanone (136 mg, 0.332 mmol) in THF (5 mL) was added TBAF (332 μL, 1.0 N in THF, 0.332 mmol, 1.0 eq.). After 1 hour at 25° C., the reaction mixture was partitioned between saturated NaHCO3 aqueous solution and CH2Cl2, the aqueous layer was extracted with CH2Cl2 and the organic layers were dried and concentrated to yield crude product. The crude product was purified by chromatography to yield the title compound as a yellow solid.

Workup

  1. customthe reaction mixture was partitioned between saturated NaHCO3 aqueous solution and CH2Cl2
  2. extractionthe aqueous layer was extracted with CH2Cl2
  3. customthe organic layers were dried
  4. concentrationconcentrated
  5. customto yield crude product
  6. customThe crude product was purified by chromatography

Sources & evidence

ORD record
ord-3868626d36a14821ae7fcea00e5f2fba
Source dataset
uspto-grants-2012_11
Patent number
US08318766B2

Reaction notes

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