Tetrahydrofuran → Rac-4-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-3,5-dimethyl-benzonitrile

HRID 1958779Notes

Reaction equation

HRID 1958779 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH3:11])[C:9]=1[OH:10])[C:5]#[N:6].C1C=CC(P([C:25]2[CH:30]=[CH:29]C=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C([O:40][CH2:41][CH3:42])=O)=O.C1C[O:46][CH2:45]C1>C1(C)C=CC=CC=1>[CH3:25][C:30]1([CH3:29])[O:40][CH:41]([CH2:42][O:10][C:9]2[C:8]([CH3:11])=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=2[CH3:1])[CH2:45][O:46]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 201763,5-Dimethyl-4-hydroxybenzonitrileHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 66692495Rac-4-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-3,5-dimethyl-benzonitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3,5-dimethyl-4-hydroxy-benzonitrile (5.0 g, 34.0 mmol) in THF (40 mL), rac-(2,2-dimethyl-[1,3]dioxolan-4-yl)-MeOH (4.49 g, 34.0 mmol) followed by PPh3 (13.4 g, 50.9 mmol) was added. The mixture was cooled with an ice-bath before DEAD (8.87 g, 50.9 mmol, 23.4 mL of a 40% solution in toluene) was added dropwise. The mixture was stirred at rt for 1 h, the solvent was removed in vacuo and the residue was purified by CC eluting with Hept:EA 99:1 to 92:8 to give rac-4-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-3,5-dimethyl-benzonitrile as a pale yellow oil (7.20 g). LC-MS: tR=0.99 min, [M+1]+=not detected.

Workup

  1. additionwas added
  2. additionwas added dropwise
  3. customthe solvent was removed in vacuo
  4. customthe residue was purified by CC
  5. washeluting with Hept

Sources & evidence

ORD record
ord-7253e326bbb94a6d81c95bc74f37478f
Source dataset
uspto-grants-2013_04
Patent number
US08410151B2

Reaction notes

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