Diethyl Ether → HCID 57881436, compound

HRID 1878396Notes

Reaction equation

HRID 1878396 reaction equation
[CH:1]([Mg]Br)([CH3:3])[CH3:2].C(OCC)C.[CH:11]([C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[C:16]#[N:17])=[O:12]>O1CCCC1>[OH:12][CH:11]([C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[C:16]#[N:17])[CH:1]([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 90670m-FormylbenzonitrileHCID 178418365HCID 178418365, compound

Product 1

HCID 57881436HCID 57881436, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

15% Isopropyl magnesium bromide in diethyl ether (23.5 mL, 24.0 mmol) was added to a stirred solution of 3-formylbenzonitrile (2.62 mg, 20.0 mmol) in dry tetrahydrofuran (18 mL), at 0° C. under a nitrogen atmosphere. After stirring at 0° C. for 1 hour, then at room temperature for 2 hours, the mixture was partitioned between ethyl acetate and 1M hydrochloric acid. The aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with brine, dried over sodium sulfate and concentrated under vacuum. The residue was purified with silica column chromatography (eluting with 9% to 25% ethyl acetate in heptane) to afford the title compound (1.164 g).

Workup

  1. waitat room temperature for 2 hours
  2. customthe mixture was partitioned between ethyl acetate and 1M hydrochloric acid
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified with silica column chromatography (eluting with 9% to 25% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-241d5828c1d24cc3bc6caf0afdcef425
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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