Toluene → 3-Ethyl-5-methyl-4-oxiranylmethoxy-benzonitrile

HRID 245090Notes

Reaction equation

HRID 245090 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([CH3:12])[C:10]=1[OH:11])[C:6]#[N:7])[CH3:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH2:32]1[O:34][C@@H:33]1[CH2:35]O.CCOC(/N=N/C(OCC)=O)=O.C1(C)C=CC=CC=1>C1COCC1>[CH2:1]([C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([CH3:12])[C:10]=1[O:11][CH2:35][CH:33]1[CH2:32][O:34]1)[C:6]#[N:7])[CH3:2]

Participants

7

Reactant 5

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 5460455(+)-GlycidolHCID 5462977Diethyl azodicarboxylateHCID 597599503-Ethyl-4-hydroxy-5-methylbenzonitrile

Product 1

HCID 866453003-Ethyl-5-methyl-4-oxiranylmethoxy-benzonitrileYield 85.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-ethyl-4-hydroxy-5-methyl-benzonitrile (5.06 g, 31.4 mmol) in THF (80 mL), PPh3 (9.06 g, 34.5 mmol) and (R)-glycidol (2.29 mL, 34.5 mmol) are added. The mixture is cooled to 0° C. before DEAD in toluene (15.8 mL, 34.5 mmol) is added. The mixture is stirred for 18 h while warming up to rt. The solvent is evaporated and the crude product is purified by CC on silica gel eluting with heptane:EA 7:3 to give 3-ethyl-5-methyl-4-oxiranylmethoxy-benzonitrile (5.85 g) as a yellow oil; LC-MS: tR=0.96 min; [M+42]+=259.08.

Workup

  1. additionis added
  2. customThe solvent is evaporated
  3. customthe crude product is purified by CC on silica gel eluting with heptane:EA 7:3

Sources & evidence

ORD record
ord-126c6d92c9ea4080969fd132b499f691
Source dataset
uspto-grants-2014_02
Patent number
US08658675B2

Reaction notes

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