Triphenylphosphine → HCID 21949861, compound

HRID 2215331Notes

Reaction equation

HRID 2215331 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[CH2:41]([C:43]1[C:47]([O:48][C:49]2[CH:50]=[C:51]([CH:54]=[C:55]([F:57])[CH:56]=2)[C:52]#[N:53])=[C:46]([CH2:58][CH2:59]O)[NH:45][N:44]=1)[CH3:42]>O1CCCC1>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([O:1][CH2:42][CH2:41][C:43]2[NH:44][N:45]=[C:46]([CH2:58][CH3:59])[C:47]=2[O:48][C:49]2[CH:50]=[C:51]([CH:54]=[C:55]([F:57])[CH:56]=2)[C:52]#[N:53])=[CH:3][CH:4]=1)#[N:7]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 130194-CyanophenolHCID 5462977Diethyl azodicarboxylateHCID 21949766HCID 21949766, compound

Product 1

HCID 21949861HCID 21949861, compoundYield 49.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Hydroxy-benzonitrile (49 mg, 0.41 mmol), triphenylphosphine (106 mg, 0.41 mmol) and diethylazodicarboxylate (65 μl, 0.41 mmol) were added sequentially to a solution of the alcohol from Example 148 (74 mg, 0.27 mmol) in tetrahydrofuran (2 ml) under nitrogen at 0° C. The reaction was allowed to warm to room temperature and was stirred for 18 hours. The mixture was concentrated under reduced pressure and purified by flash chromatography on silica gel eluting with toluene:ethyl acetate (75:25, by volume) to provide the title compound (50 mg) as a yellow oil.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. custompurified by flash chromatography on silica gel eluting with toluene:ethyl acetate (75:25, by volume)

Sources & evidence

ORD record
ord-48da1c68247a4a30aa17e38bc37a93f7
Source dataset
uspto-grants-2006_09
Patent number
US07109228B2

Reaction notes

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