Phenol → HCID 86620289, compound

HRID 503663Notes

Reaction equation

C1(O)C=CC=CC=1.[C:8]1([P:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[N:27]([C:35]([O:37]C(C)C)=[O:36])=[N:28][C:29]([O:31]C(C)C)=[O:30].N(C(OCC)=O)=NC(OCC)=O>C1COCC1.CCOC(C)=O.O>[C:21]1([P:14]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1.[N:27]([C:35]([O-:37])=[O:36])=[N:28][C:29]([O-:31])=[O:30]

Participants

Conditions

Temperature: 0 °C

Procedure

The substrate phenol or carboxylic acid is dissolved in THF (0.05-0.5 M) and chilled to 0° C. Triphenylphosphine (1-4 eq), alcohol (1-4 eq) and diisopropyl azodicaroxylate (DIAD) or diethyl azodicarboxylate (DEAD) (1-4 eq) were added, in turn. The reaction was stirred overnight with gradual warming to rt. The reaction mixture is diluted with EtOAc/water and the layers were separated. The aqueous layer is further extracted with EtOAc. The organic layers were combined and washed with water and brine and dried over Na2SO4. The mixture is concentrated in vacuo to give the crude product, which was purified by flash chromatography on silica gel to afford the coupling product.

Workup

temperaturewith gradual warming to rt
customthe layers were separated
extractionThe aqueous layer is further extracted with EtOAc
washwashed with water and brine
dry with materialdried over Na2SO4
concentrationThe mixture is concentrated in vacuo

Sources & evidence

ORD record: ord-04e6afe55e064e47b27cad3df3d2f8d2
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07776919B2

Reaction notes

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