Triphenylphosphine → t-Butoxycarbonylamino-3-[2-(4-cyanophenyl)ethoxy]-2-methylbenzene

HRID 1791853Notes

Reaction equation

HRID 1791853 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[C:32]([O:36][C:37]([NH:39][C:40]1[C:41]([CH3:47])=[C:42]([OH:46])[CH:43]=[CH:44][CH:45]=1)=[O:38])([CH3:35])([CH3:34])[CH3:33].[C:48]([C:50]1[CH:55]=[CH:54][C:53]([CH2:56][CH2:57]O)=[CH:52][CH:51]=1)#[N:49]>C1COCC1.O>[C:32]([O:36][C:37]([NH:39][C:40]1[CH:45]=[CH:44][CH:43]=[C:42]([O:46][CH2:57][CH2:56][C:53]2[CH:54]=[CH:55][C:50]([C:48]#[N:49])=[CH:51][CH:52]=2)[C:41]=1[CH3:47])=[O:38])([CH3:35])([CH3:34])[CH3:33]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 28008154-(2-Hydroxyethyl)benzonitrileHCID 5462977Diethyl azodicarboxylateHCID 220334873-t-Butoxycarbonylamino-2-methylphenol

Product 1

HCID 22033517t-Butoxycarbonylamino-3-[2-(4-cyanophenyl)ethoxy]-2-methylbenzeneYield 77%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Triphenylphosphine (1.31 g, 13.5 mmol) and diethylazodicarboxylate (1.7 mL) were dissolved in THF (20 mL) under nitrogen. After 15 minutes 3-t-butoxycarbonylamino-2-methylphenol (2.48 g; 11.1 mmol; from step (i) above) dissolved in THF (20 mL) and 2-(4-cyanophenyl)ethanol (1.9 g, 13 mmol) were added. After 5 days at room temperature water was added and the stirring continued for 30 minutes. The mixture was extracted with EtOAc. The organic phase was washed with water and brine, dried (MgSO4) and the solvent removed in vacuo. Purification by flash chromatography afforded 2.98 g (77%) of the sub-title compound.

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customPurification by flash chromatography

Sources & evidence

ORD record
ord-6be99bc338074bd19cfef980b50197e0
Source dataset
uspto-grants-2006_07
Patent number
US07074820B2

Reaction notes

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