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

HRID 1186971Notes

Reaction equation

HRID 1186971 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-e8882d231a2c4d61a9b82fa785bd576d
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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