Triphenylphosphine → HCID 21874907, compound

HRID 723660

Reaction equation

HRID 723660 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1C=CC(COC(/N=N/C(OCC2C=CC=CC=2)=O)=O)=CC=1.[F:42][C:43]([F:52])([F:51])[C:44]1[CH:49]=[CH:48][C:47]([OH:50])=[CH:46][CH:45]=1.[CH3:53][C:54]1[O:58][C:57]([CH2:59][CH2:60]O)=[CH:56][CH:55]=1>C1COCC1>[CH3:53][C:54]1[O:58][C:57]([CH2:59][CH2:60][O:50][C:47]2[CH:46]=[CH:45][C:44]([C:43]([F:51])([F:52])[F:42])=[CH:49][CH:48]=2)=[CH:56][CH:55]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 678744-(Trifluoromethyl)phenolHCID 5387121Dibenzyl azodicarboxylateHCID 110623902-(5-Methylfuran-2-yl)ethan-1-ol

Product 1

HCID 21874907HCID 21874907, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of triphenylphosphine (1.56 g, 5.95 mmol) in THF (40 mL) was added DBAD (1,37 g, 5.95 mmol). After 10 min, 4-trifluoromethylphenol (0.964 g, 5.95 mmol) was added. After 10 additional minutes, compound 21A (0.500 g, 3.97 mmol) was added. After 14 h at 25° C., the reaction was concentrated in vacuo and purified by flash chromatography on silica eluting with chloroform to give 0.713 g (44%) of compound 232A as a clear oil.

Workup

  1. waitAfter 14 h at 25° C.
  2. concentrationthe reaction was concentrated in vacuo
  3. custompurified by flash chromatography on silica eluting with chloroform

Sources & evidence

ORD record
ord-51fc584def8f4673823bbd81a5c2553b
Source dataset
uspto-grants-2006_11
Patent number
US07141578B2

Linked notes

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