Diphenylphosphine → HCID 90415270, compound

HRID 57383Notes

Reaction equation

HRID 57383 reaction equation
C1(PC2C=CC=CC=2)C=CC=CC=1.[N:14]([CH:17]([C:19]1[O:20][C:21]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)=[C:22]([CH3:24])[N:23]=1)[CH3:18])=[N+]=[N-]>CO>[Cl:31][C:28]1[CH:27]=[CH:26][C:25]([C:21]2[O:20][C:19]([CH:17]([NH2:14])[CH3:18])=[N:23][C:22]=2[CH3:24])=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 70017DiphenylphosphineHCID 904151212-(1-Azidoethyl)-5-(4-chlorophenyl)-4-methyloxazole

Product 1

HCID 90415270HCID 90415270, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

SiliaBond® Diphenylphosphine (1500 mg, 1.19 mmol/g) was added to a solution of 2-(1-azidoethyl)-5-(4-chlorophenyl)-4-methyloxazole (366 mg, 1.393 mmol) in anhydrous methanol (15 ml) and shaken for 3 hours. The reaction was filtered and concentrated in vacuo. Flash column chromatography (silica, 40 g) eluting with 2-10% MeOH/DCM afforded 160 mg (white solid). HRMS(B) tR=1.73 min; MS m/z 236.0716

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated in vacuo
  3. washFlash column chromatography (silica, 40 g) eluting with 2-10% MeOH/DCM
  4. customafforded 160 mg (white solid)

Sources & evidence

ORD record
ord-03856303fa484d6eb768a8b464c01e01
Source dataset
uspto-grants-2016_09
Patent number
US09434719B2

Reaction notes

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