2-(Methyloxy)-4-(2-oxoethyl)benzonitrile → 4-(2-Hydroxypropyl)-2-methoxybenzonitrile

HRID 1519535Notes

Reaction equation

HRID 1519535 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([CH2:11][CH:12]=[O:13])[CH:8]=[CH:7][C:4]=1[C:5]#[N:6].[CH3:14][Mg]Br>ClCCl.C1COCC1>[OH:13][CH:12]([CH3:14])[CH2:11][C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[C:3]([O:2][CH3:1])[CH:10]=1

Participants

5

Reactant 2

HCID 772312592-(Methyloxy)-4-(2-oxoethyl)benzonitrileHCID 178418573HCID 178418573, compound

Product 1

HCID 666438784-(2-Hydroxypropyl)-2-methoxybenzonitrile

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1.48 g (8.47 mmol) of 2-methoxy-4-(2-oxoethyl)benzonitrile in dichloromethane (30 mL) at 0° C. was added 2.82 mL (8.47 mmol) of a 3.0 M solution of methylmagnesium bromide in THF. The reaction mixture was allowed to warm up to RT and stirred for 12 h. The reaction was then quenched by the addition of 10 mL of 1 N hydrochloric acid and extracted with dichloromethane (2×30 mL). The combined organic extracts were dried with magnesium sulfate, filtered, and concentrated in vacuo. The crude residue was purified on silica (30% EtOAc/hexanes as eluent) to afford 4-(2-hydroxypropyl)-2-methoxybenzonitrile as a clear liquid. 1H NMR (500 MHz, CDCl3) δ 7.47 (d, 1H, J=7.8 Hz), 6.85 (dd, 1H, J=3.4 Hz), 6.82 (s, 1H), 4.05 (m, 1H), 3.93 (d, 2H), 3.91 (s, 3H), 1.25 (d, 2H, J=6.1 Hz). LC-MS (IE, m/z): 192.3 [M+1)+.

Workup

  1. customThe reaction was then quenched by the addition of 10 mL of 1 N hydrochloric acid
  2. extractionextracted with dichloromethane (2×30 mL)
  3. dry with materialThe combined organic extracts were dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified on silica (30% EtOAc/hexanes as eluent)

Sources & evidence

ORD record
ord-eee5be627e2d4523b156bed1745c7d41
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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