Triacetoxyperiodinane → 2-(Methyloxy)-4-(2-oxoethyl)benzonitrile

HRID 1474230Notes

Reaction equation

HRID 1474230 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[C:6]([O:12][CH3:13])[CH:5]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH3:13][O:12][C:6]1[CH:5]=[C:4]([CH2:3][CH:2]=[O:1])[CH:11]=[CH:10][C:7]=1[C:8]#[N:9]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 542351984-(2-Hydroxyethyl)-2-methoxybenzonitrile

Product 1

HCID 772312592-(Methyloxy)-4-(2-oxoethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-(2-hydroxyethyl)-2-methoxybenzonitrile (1.5 g, 8.5 mmol) in dry CH2Cl2 (30 mL) at 0° C. was added Dess-Martin periodinane (3.6 g, 8.5 mmol) in one portion. The mixture was stirred for 12 h at rt and quenched with a 1:1 mixture of saturated Na2S2O3 (40 mL) and saturated NaHCO3 (40 mL). The resulting mixture was diluted with CH2Cl2 (70 mL) and the layers were separated. The aqueous phase was extracted with CH2Cl2 (2×50 mL). The combined organic phases were washed with brine, dried (Na2SO4), and concentrated in vacuo to give 2-methoxy-4-(2-oxoethyl)benzonitrile. The residue was used in the next step without further purification. 1H NMR (500 MHz, CDCl3) δ 9.77 (s, 1H), 7.52 (d, 1H, J=8.8 Hz), 6.86 (dd, 1H, J=1.1 Hz), 6.79 (s, 1H), 3.92 (s, 3H), 3.76 (s, 2H); LCMS: [(M+1)]+=176.26; tR=1.98 min.

Workup

  1. customquenched with a 1:1 mixture of saturated Na2S2O3 (40 mL) and saturated NaHCO3 (40 mL)
  2. additionThe resulting mixture was diluted with CH2Cl2 (70 mL)
  3. customthe layers were separated
  4. extractionThe aqueous phase was extracted with CH2Cl2 (2×50 mL)
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4c7914f55e58469eb83edb5d6fd5b096
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

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