Hydrochloric Acid → 908269-77-2

HRID 1446695Notes

Reaction equation

HRID 1446695 reaction equation
I[C:2]1[CH:3]=[C:4]([C:8](=[O:13])[C:9]([CH3:12])([CH3:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1.C(=[NH:27])(C1C=CC=CC=1)C1C=CC=CC=1.CC([O-])(C)C.[Na+].Cl.[OH-].[Na+].[Cl-].[Na+]>C(OCC)(=O)C.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C1COCC1>[NH2:27][C:2]1[CH:3]=[C:4]([C:8](=[O:13])[C:9]([CH3:12])([CH3:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 136809Benzophenone imineHCID 23676156Sodium t-butoxideHCID 68541861HCID 68541861, compound

Product 1

HCID 58087019908269-77-2Yield 82%

Reagents, catalysts & solvents 3

HCID 634876Binap, (A+-)-CatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

Combine 1-(3-iodo-phenyl)-2,2-dimethyl-propan-1-one (2.0 g, 8.3 mmol), benzophenone imine (1.7 mL, 1.2 equiv.), racemic BINAP (0.23 g, 4.5 mol %), NaOtBu (1.1 g, 1.4 equiv.), and THF (30 mL). De-gas thoroughly with nitrogen then add bis(dibenzylideneacetone) palladium (0.14 g, 3 mol %) and place under nitrogen. Heat the reaction at 50° C. overnight. The next morning add approximately 8 mL 5 N HCl (aq) and heat for an additional hour at 50° C. Let cool to room temperature then dilute with ethyl acetate and make basic with 1 N NaOH (aq). Wash organics with aqueous saturated sodium chloride. Dry over magnesium sulfate, filter and concentrate in vacuo. Purify by silica chromatography (Hex→9:1 Hex:EtOAc→4:1 Hex:EtOAc) to give a yellow residue (1.2 g, 82%). MS (ES), m/z 178 (M+1).

Workup

  1. customDe-gas thoroughly with nitrogen
  2. temperatureHeat
  3. customthe reaction at 50° C. overnight
  4. temperatureLet cool to room temperature
  5. dry with materialDry over magnesium sulfate
  6. filtrationfilter
  7. concentrationconcentrate in vacuo
  8. customPurify by silica chromatography (Hex→9:1 Hex:EtOAc→4:1 Hex:EtOAc)

Sources & evidence

ORD record
ord-20b2359d2e044c468494120339573e82
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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