Phenol → HCID 86620289, compound

HRID 30539Notes

Reaction equation

HRID 30539 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:32]([O-:34])=[O:33])=[N:28][C:29]([O-:31])=[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:32]([O-:34])=[O:33])=[N:28][C:29]([O-:31])=[O:30]

Participants

7

Reactant 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 51573101N-carboxylatoiminocarbamate

Product 1

HCID 86620289HCID 86620289, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 22728543Water ethylacetateSolvent

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 duisopropyl 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

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

Sources & evidence

ORD record
ord-8a114fd383b841f4bf7e87adabf96043
Source dataset
uspto-grants-2008_09
Patent number
US07423177B2

Reaction notes

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