Triphenylphosphine → HCID 86594117, compound

HRID 1375678Notes

Reaction equation

HRID 1375678 reaction equation
NC1C(C(OCC)=O)=NOC=1C1C=CC=C(/C=C/CO)C=1.[OH:22][C:23]1[CH:32]=[CH:31][CH:30]=[C:29](O)[C:24]=1C(OC)=O.[CH:34]1[CH:39]=[CH:38][C:37]([P:40]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[CH:36][CH:35]=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:23]1([O-:22])[CH:32]=[CH:31][CH:30]=[CH:29][CH:24]=1.[CH:50]1[CH:49]=[CH:48][C:47]([P:40]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:37]2[CH:38]=[CH:39][CH:34]=[CH:35][CH:36]=2)=[CH:52][CH:51]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 519869Methyl 2,6-dihydroxybenzoateHCID 5462977Diethyl azodicarboxylateHCID 69507779HCID 69507779, compound

Product 1

HCID 86594117HCID 86594117, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a THF (1 mL) solution of compound from Example 21D (150 mg, 0.52 mmol), methyl 2,6-dihydroxybenzoate (336 mg, 2.0 mmol), and PPh3 (210 mg, 0.8 mmol) was added DEAD (140 mg, 0.8 mmol) at 0° C. Insoluble salt (phenolate/PPh3) formed quickly. The mixture was warmed to ambient temperature and dichloromethane (3 mL) was added, but the salt remained insoluble in this solvent system. A drop of water was added after 2 hours to decompose the salt, upon which the slurry turned into a homogeneous solution. The mixture was purified by flash column chromatography (30% ethyl acetate in hexanes) to provide the titled compound (130 mg, 40%).

Sources & evidence

ORD record
ord-2602ca6e4b504d38a7677ede6110d59e
Source dataset
uspto-grants-2007_01
Patent number
US07169797B2

Reaction notes

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