Potassium Sodium Tartrate → HCID 59770442, compound

HRID 2218771Notes

Reaction equation

HRID 2218771 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=O)[C:10]3[CH:13]=[CH:14][CH:15]=[N:16][C:9]=3[CH2:8][O:7][C:6]=2[CH:17]=1.[C@H:18](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>[CH3-].C[Al+]C.[CH-]1C=CC=C1.[CH-]1C=CC=C1.[Cl-].[Ti+3].O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[CH2:18])[C:10]3[CH:13]=[CH:14][CH:15]=[N:16][C:9]=3[CH2:8][O:7][C:6]=2[CH:17]=1

Participants

5

Reactant 2

HCID 9357Potassium Sodium TartrateHCID 10443785HCID 10443785, compound

Product 1

HCID 59770442HCID 59770442, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 53384502mu-Chlorobis(eta5-cyclopentadienyl)(dimethylaluminum)-mu-methylenetitaniumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Combine 8-fluoro-11H-10-oxa-1-aza-dibenzo[a,d]cyclohepten-5-one (567 mg, 2.47 mmol) and anhydrous tetrahydrofuran (25 mL). Chill the solution to 0° C. and add Tebbe reagent (0.5M/L solution in toluene, 5.4 mL, 2.72 mmol). Remove cooling and stir the admixture for 10 min. Quench the reaction by adding saturated aqueous Rochelle's salt solution (75 mL). Stir the biphasic mixture rapidly for 10 min, then separate the layers and extract the aqueous layer with ethyl acetate. Dry the combined organic layers with magnesium sulfate, filter and strip. Purify the crude product by flash chromatography (25% ethyl acetate/hexanes) to provide 416 mg(74%) of purified product. LCMS (APCI-pos): 228.1 (M+H). LCMS (APCI-neg): 226.9 (M−H).

Workup

  1. customRemove
  2. temperaturecooling
  3. customQuench
  4. customthe reaction
  5. stirringStir the biphasic mixture rapidly for 10 min
  6. customseparate the layers
  7. extractionextract the aqueous layer with ethyl acetate
  8. dry with materialDry the combined organic layers with magnesium sulfate
  9. filtrationfilter
  10. customPurify the crude product by flash chromatography (25% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-2188fa770d2a4104b6af670034e6cacc
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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