Triphenylphosphine → HCID 67302000, compound

HRID 1015368Notes

Reaction equation

HRID 1015368 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH:9]([OH:12])[CH2:8][CH2:7]1)=[O:5])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[C:34]=1O.N(C(OCC)=O)=NC(OCC)=O>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH:9]([O:12][C:34]2[C:33]([F:32])=[CH:38][CH:37]=[CH:36][C:35]=2[F:39])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 86973Ethyl 4-hydroxycyclohexanecarboxylateHCID 943922,6-DifluorophenolHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 67302000HCID 67302000, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

4-Hydroxycyclohexanecarboxylic acid ethyl ester (300 mg; 1.7 mmol), triphenylphosphine (1 g; 4.2 mmol) and 2,6-difluorophenol (340 mg; 2.6 mmol) were stirred in anhydrous toluene and chilled to 0° C. under nitrogen flow. Diethyl azodicarboxylate (2 mL; 4.3 mmol) was added to the mixture over 1 minute and warmed to room temperature. Reaction continued for 16 hours. Reaction was quenched with water, and mixture was extracted with 4×5 mL with ethyl acetate. Combined organics were washed with brine and dried over MgSO4. Oily residue was triturated with diethyl ether and solids filtered off. Filtrate was concentrated at reduced pressure and purified via flash chromatography using 5-20% ethyl acetate in hexanes to give 162 mg of title compound. (34% yield).

Workup

  1. temperaturewarmed to room temperature
  2. customReaction
  3. customReaction
  4. customwas quenched with water, and mixture
  5. extractionwas extracted with 4×5 mL with ethyl acetate
  6. washCombined organics were washed with brine
  7. dry with materialdried over MgSO4
  8. customOily residue was triturated with diethyl ether and solids
  9. filtrationfiltered off
  10. concentrationFiltrate was concentrated at reduced pressure
  11. custompurified via flash chromatography

Sources & evidence

ORD record
ord-eda9ecee2a4f4c428c61ec6e30987edd
Source dataset
uspto-grants-2011_07
Patent number
US07985755B2

Reaction notes

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