Triphenylphosphine → HCID 71239540, compound

HRID 1403192Notes

Reaction equation

HRID 1403192 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.Cl.[CH3:35][N:36]1[CH2:41][CH2:40][CH:39]([OH:42])[CH2:38][CH2:37]1.[C:43]([C:45]1[CH:46]=[C:47](O)[CH:48]=[CH:49][CH:50]=1)#[CH:44]>C(Cl)Cl>[C:43]([C:45]1[CH:50]=[C:49]([CH:48]=[CH:47][CH:46]=1)[O:42][CH:39]1[CH2:40][CH2:41][N:36]([CH3:35])[CH2:37][CH2:38]1)#[CH:44]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 139144m-EthynylphenolHCID 5363146Diisopropyl azodicarboxylateHCID 2231710780154-05-8

Product 1

HCID 71239540HCID 71239540, compoundYield 39.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Ph3P (1.32 g, 5.04 mmol) in DCM (4 mL), under a nitrogen atmosphere, was cooled with an ice bath and treated with neat DIAD (397 μL, 4.6 mmol). After 25 min the solution was added drop wise to 1-methylpiperidin-4-ol hydrochloride (547 g, 4.6 mmol) and 3-ethynylphenol (277 μL, 4.2 mmol) in DCM (8 mL), cooled with an ice bath, under a nitrogen atmosphere, with stirring. The reaction was then stirred at room temperature 4 h. The volatiles were partially removed by evaporation and the residue was purified by flash chromatography (DCM/MeOH 95/5) affording the title compound as a colorless oil (360 mg, 39%).

Workup

  1. temperaturecooled with an ice bath, under a nitrogen atmosphere
  2. stirringThe reaction was then stirred at room temperature 4 h
  3. customThe volatiles were partially removed by evaporation
  4. customthe residue was purified by flash chromatography (DCM/MeOH 95/5)

Sources & evidence

ORD record
ord-52d9db60895440a488e3cad5cf359c23
Source dataset
uspto-grants-2014_12
Patent number
US08912200B2

Reaction notes

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