Sodium Bicarbonate → HCID 11729267, compound

HRID 395621Notes

Reaction equation

HRID 395621 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([N:27]3[CH:31]=[CH:30][N:29]=[C:28]3[CH3:32])[O:11][C:12]=2[CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23]C(C)C)=[CH:4][CH:3]=1.C(=O)([O-])O.[Na+]>[Ti](Cl)(Cl)(Cl)Cl.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([N:27]3[CH:31]=[CH:30][N:29]=[C:28]3[CH3:32])[O:11][C:12]=2[CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[OH:23])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 11080898HCID 11080898, compound

Product 1

HCID 11729267HCID 11729267, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 4-(4-chlorophenyl)-2-(2-methyl-1-imidazolyl)-5-[3-[2-(2-propyloxy)phenoxy]propyl]oxazole (200 mg), titanium(IV) chloride (380 mg) and methylene chloride (5 ml) was stirred at 0° C. for 1 hour. The reaction mixture was poured into a saturated aqueous solution of sodium hydrogen carbonate (10 ml) and extracted with ethyl acetate (10 ml×2). The organic layer was dried over anhydrous magnesium sulfate and then concentrated, and the residue was recrystallized from acetone-isopropyl ether to give 4-(4-chlorophenyl)-5-[3-(2-hydroxyphenoxy)propyl]-2-(2-methyl-1-imidazolyl)oxazole as colorless prisms (90 mg, 51%). Melting point 110-111° C.

Workup

  1. extractionextracted with ethyl acetate (10 ml×2)
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. customthe residue was recrystallized from acetone-isopropyl ether

Sources & evidence

ORD record
ord-fd0960179f024c0182193b190eee07f3
Source dataset
uspto-grants-2003_08
Patent number
US06605629B1

Reaction notes

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