Triphenylphosphine → 2-(3-(2,6-Dimethylbenzyloxy)phenyl)acetonitrile

HRID 1958840Notes

Reaction equation

HRID 1958840 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]#[N:10])[CH:5]=[CH:6][CH:7]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[CH3:25][C:26]1[CH:33]=[CH:32][CH:31]=[C:30]([CH3:34])[C:27]=1[CH2:28]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH3:25][C:26]1[CH:33]=[CH:32][CH:31]=[C:30]([CH3:34])[C:27]=1[CH2:28][O:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]#[N:10])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 186748(2,6-Dimethylphenyl)methanolHCID 137810422-(3-Hydroxyphenyl)acetonitrile

Product 1

HCID 669594102-(3-(2,6-Dimethylbenzyloxy)phenyl)acetonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-(3-Hydroxyphenyl)acetonitrile (Step A, 5 g, 37 mmol) and diisopropyl azodicarboxylate (DIAD, 3.38 g, 16.7 mmol) in dry THF (20 ml) was added drop wise to a solution of 2,6-Dimethylbenzyl alcohol (2.25 g, 16.5 mmol) and triphenylphosphine (TPP, 4.3 g, 16.4 mmol) in THF (30 ml) at 0° C. under argon. The reaction mixture was stirred at room temperature for 16 hours or until all the starting material is consumed. Silica gel (25 g) was added to the mixture, solvents were removed under reduced pressure, loaded on silica gel column and eluted with methylene chloride:hexane (1:1) to give light yellow crystalline solid.

Workup

  1. customis consumed
  2. additionSilica gel (25 g) was added to the mixture, solvents
  3. customwere removed under reduced pressure
  4. washeluted with methylene chloride:hexane (1:1)
  5. customto give light yellow crystalline solid

Sources & evidence

ORD record
ord-87d0e1535a3e4b1c8f867deefb1666a0
Source dataset
uspto-grants-2013_04
Patent number
US08410154B2

Reaction notes

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