Carbon Tetrachloride → HCID 59451377, compound

HRID 1874855Notes

Reaction equation

HRID 1874855 reaction equation
[C:1]([CH:3]([NH:13][C:14](=O)[CH:15]([CH3:17])[CH3:16])[CH2:4][O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)#[N:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:39]>C(#N)C>[Cl:39][C:1]1[N:2]=[C:14]([CH:15]([CH3:17])[CH3:16])[NH:13][C:3]=1[CH2:4][O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 59451364HCID 59451364, compound

Product 1

HCID 59451377HCID 59451377, compoundYield 41.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of N-{1-cyano-2-[(phenylmethyl)oxy]ethyl}-2-methylpropanamide (1.60 g, 6.5 mmol), triphenylphosphine (4.2 g, 16.0 mmol), and carbon tetrachloride (1.6 mL, 16.6 mmol) in acetonitrile (65 mL) was heated at 45° C. for 4.5 h. The reaction was concentrated and the residue was stirred in CH2Cl2 (70 mL) and 0.5 N NaOH (60 mL) for 10 min. The organic layer was isolated, dried (Na2SO4), filtered, concentrated and the residue was purified by silica gel flash column chromatography (5-50% EtOAc:hexanes) to give the title compound (0.710 g, 41%) as a yellow oil. 1H NMR (400 MHz, CDCl3) δ ppm 10.69 (br. s., 1H), 7.28-7.36 (m, 5H), 4.51 (s, 2H), 4.48 (s, 2 H), 2.92 (sept, 1H), 1.24 (d, 6H).

Workup

  1. concentrationThe reaction was concentrated
  2. customThe organic layer was isolated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe residue was purified by silica gel flash column chromatography (5-50% EtOAc:hexanes)

Sources & evidence

ORD record
ord-4831ccb4a355483ea4903073a32d9d4d
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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