Ethyl Acetate → HCID 58075658, compound

HRID 2370226Notes

Reaction equation

HRID 2370226 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH:9]=[O:10])=[C:4]([C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH2:12])[N:3]=1.[CH:19]([Mg]Br)=[CH2:20].[NH4+].[Cl-].C(OCC)(=O)C>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH:9]([OH:10])[CH:19]=[CH2:20])=[C:4]([C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH2:12])[N:3]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 58075698HCID 58075698, compoundHCID 178418507HCID 178418507, compound

Product 1

HCID 58075658HCID 58075658, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 2,4-dichloro-6-(1-phenylvinyl)pyrimidine-5-carbaldehyde (200 mg) in THF (3.6 mL) at −78 C was added vinylmagnesium bromide (0.79 mL, 1M solution in THF) dropwise, and the reaction mixture was stirred at −78° C. for 20 min. Saturated NH4Cl was added followed by ethyl acetate, the aqueous layer was extracted with ethyl acetate (×3), and the combined organic layers were dried over anhydrous sodium sulfate and then filtered. The filtrate was concentrated in vacuo to give the title compound (156 mg) as a colorless oil. The crude product was used directly for the next step.

Workup

  1. extractionthe aqueous layer was extracted with ethyl acetate (×3)
  2. dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-3a778edc7a9243ee89c64d1af5d963ac
Source dataset
uspto-grants-2014_04
Patent number
US08710061B2

Reaction notes

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