3-Acetylbenzonitrile → 317829-69-9

HRID 2300767Notes

Reaction equation

HRID 2300767 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[C:7]#[N:8])(=[O:3])[CH3:2]>C(Cl)Cl>[C:7]([C:6]1[CH:5]=[C:4]([C@H:1]([OH:3])[CH3:2])[CH:11]=[CH:10][CH:9]=1)#[N:8]

Participants

3

Reactant 1

HCID 802223-Acetylbenzonitrile

Product 1

HCID 51886734317829-69-9Yield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (S)-oxazaborolidine (3.44 mmol) in CH2Cl2 (3.5 mL) at −20° C. was added a solution of 3-acetylbenzonitrile (3.47 mmol) in CH2Cl2 (3.5 mL) over a period of approximately 30 minutes. The mixture was then allowed to warm to room temperature for 1 hour then quenched by transferring to a stirred flask of methanol at −20° C. The resultant mixture was concentrated under reduced pressure and the residue taken up in methanol and concentrated twice more and dried overnight under high vacuum. This residue was purified on silica gel chromatography (70:30 hexanes:ethyl acetate) to yield the title compound (373 mg). 1H NMR (500 MHz, CDCl3): δ 7.71 (m, 1H); 7.63 (d, J=7.8 Hz, 1H); 7.58 (m, 1H); 7.48 (t, J=7.7 Hz, 1H); 4.97 (m, 1H); 1.90 (d, J=3.9 Hz,, 1H); 1.53 (d, J=6.6 Hz, 3H).

Workup

  1. customthen quenched
  2. customby transferring to a stirred flask of methanol at −20° C
  3. concentrationThe resultant mixture was concentrated under reduced pressure
  4. concentrationconcentrated twice more
  5. customdried overnight under high vacuum
  6. customThis residue was purified on silica gel chromatography (70:30 hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-6a336b6401814b5facbe50ea8cfaa1c2
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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