Triethylamine → HCID 9880446, compound

HRID 842131Notes

Reaction equation

HRID 842131 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH2:22][CH2:23][CH2:24][OH:25])[C:5]2[O:9][C:8]([CH2:10][C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=3)=[N:7][C:6]=2[CH:21]=1.C(N(CC)CC)C>C1COCC1.[Pd]>[CH3:20][O:19][C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][C:14]=1[O:17][CH3:18])[CH2:10][C:8]1[O:9][C:5]2[C:4]([CH2:22][CH2:23][CH2:24][OH:25])=[CH:3][CH:2]=[CH:21][C:6]=2[N:7]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 10292092HCID 10292092, compound

Product 1

HCID 9880446HCID 9880446, compoundYield 51.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2.89 g (8.0 mmol) of 5-chloro-2-(3,4-dimethoxybenzyl)-7-(3-hydroxy-propyl)-benzoxazole in 50 ml of THF and 1.23 ml (8.8 mmol) of triethylamine and with 0.58 g of 10% Pd-C was hydrogenated in an autoclave at about 1100 psi. After 2.5 hour, the catalyst was filtered off and the solvents evaporated in vacuo. The residue was dissolved in dichloromethane and filtered through 6.3 g of silica gel in a column. The recovered material (2.53 g) was crystallized from di-isopropyl ether to give the title compound (1.36 g, 51.9%), mp 95-7° C. A second crop of 0.94 g (35.9%) was also obtained.

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe solvents evaporated in vacuo
  3. dissolutionThe residue was dissolved in dichloromethane
  4. filtrationfiltered through 6.3 g of silica gel in a column
  5. customThe recovered material (2.53 g) was crystallized from di-isopropyl ether

Sources & evidence

ORD record
ord-8be22fd3887245fc9e7797c8ae139fe0
Source dataset
uspto-grants-2002_04
Patent number
US06372770B1

Reaction notes

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