Phenol → HCID 12999576, compound

HRID 2223699Notes

Reaction equation

HRID 2223699 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:27]([N:34]1[CH2:39][CH2:38][CH:37](O)[CH2:36][CH2:35]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C1COCC1.CCOC(C)=O>[CH2:27]([N:34]1[CH2:39][CH2:38][CH:37]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:36][CH2:35]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 996PhenolHCID 11776TriphenylphosphineHCID 784611-Benzylpiperidin-4-ol

Product 1

HCID 12999576HCID 12999576, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

To a cold (0° C.) mixture of phenol (190 mg, 2.02 mmol) and triphenylphosphine (680 mg, 2.6 mmol) in dry THF (6.4 mL) is added dropwise over 30 min a solution of 1-benzyl-piperidin-4-ol (490 mg, 2.6 mmol) and diethylazadicarboxylate (0.41 mL, 2.6 mmol) in dry THF (4.8 mL). The mixture is stirred at room temperature under nitrogen for 20 h. The mixture is dissolved in EtOAc, washed with sat. NaHCO3 (2×20 mL), dried (MgSO4), filtered and concentrated to provide a crude oil. Flash chromatography (EtOAc/Hex: 3/7) provides the title compound.

Workup

  1. washwashed with sat. NaHCO3 (2×20 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto provide a crude oil

Sources & evidence

ORD record
ord-4e5df41fcac14f448cad8fc371e832d6
Source dataset
uspto-grants-2008_05
Patent number
US07375227B2

Reaction notes

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