Methyl 2-(4-formylphenoxy)acetate → Methyl [4-[2-(4,5-diphenyl-2-oxazolyl)ethenyl]phenoxy]acetate

HRID 257627Notes

Reaction equation

HRID 257627 reaction equation
[Na].[C:2]1([C:8]2[N:9]=[C:10]([CH2:19]P(=O)(OC)OC)[O:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:26]([C:28]1[CH:39]=[CH:38][C:31]([O:32][CH2:33][C:34]([O:36][CH3:37])=[O:35])=[CH:30][CH:29]=1)=O>CO.O>[C:2]1([C:8]2[N:9]=[C:10]([CH:19]=[CH:26][C:28]3[CH:39]=[CH:38][C:31]([O:32][CH2:33][C:34]([O:36][CH3:37])=[O:35])=[CH:30][CH:29]=3)[O:11][C:12]=2[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 758214Methyl 2-(4-formylphenoxy)acetateHCID 5360545SodiumHCID 54445617Dimethyl [(4,5-diphenyl-2-oxazolyl)methyl]phosphonate

Product 1

HCID 54034712Methyl [4-[2-(4,5-diphenyl-2-oxazolyl)ethenyl]phenoxy]acetate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Sodium metal (570 mg, 25 mg atom) was dissolved in methanol (50 mL) and dimethyl [(4,5-diphenyl-2-oxazolyl)methyl]phosphonate (7.80 g, 22 mmol) added. The mixture was stirred for 10 minutes before adding methyl (4-formylphenoxy)acetate (4.00 g, 20 mmol). After stirring at room temperature for 1 hour, the mixture was diluted with water and a yellow solid filtered off and air dried to give crude product (3.80 g, 44%). This was combined with 3.50 g from a previous experiment and recrystallized twice from methanol to afford analytically pure methyl [4-[2-(4,5-diphenyl-2-oxazolyl)ethenyl]phenoxy]acetate, m.p. 122°-123° C.

Workup

  1. stirringAfter stirring at room temperature for 1 hour
  2. filtrationa yellow solid filtered off
  3. customair dried
  4. customto give crude product (3.80 g, 44%)
  5. customrecrystallized twice from methanol

Sources & evidence

ORD record
ord-761c2f13d2e64d49ac15366fb37b2e95
Source dataset
uspto-grants-1993_11
Patent number
US05262540

Reaction notes

Loading…