Triphenylphosphine → HCID 21949861, compound

HRID 558289Notes

Reaction equation

HRID 558289 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-729258a4ae9d425680ecd4d942845c42
Source dataset
uspto-grants-2011_11
Patent number
US08063044B2

Reaction notes

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