Cesium carbonate → 3-{2-Formyl-4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenyl}acrylic acid tert-butyl ester

HRID 1181109Notes

Reaction equation

HRID 1181109 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15]S(C1C=CC(C)=CC=1)(=O)=O.[C:26]([O:30][C:31](=[O:43])[CH:32]=[CH:33][C:34]1[CH:39]=[CH:38][C:37](O)=[CH:36][C:35]=1[CH:41]=[O:42])([CH3:29])([CH3:28])[CH3:27].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[C:26]([O:30][C:31](=[O:43])[CH:32]=[CH:33][C:34]1[CH:39]=[CH:38][C:37]([O:15][CH2:14][CH2:13][C:3]2[N:4]=[C:5]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[O:6][C:2]=2[CH3:1])=[CH:36][C:35]=1[CH:41]=[O:42])([CH3:29])([CH3:27])[CH3:28]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 120517392-(5-Methyl-2-phenyloxazol-4-yl)ethyl 4-methylbenzenesulfonateHCID 724795753-(2-Formyl-4-hydroxyphenyl)acrylic acid tert-butyl ester

Product 1

HCID 724795833-{2-Formyl-4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenyl}acrylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

A flame-dried 100 mL round bottomed flask was charged with toluene-4-sulfonic acid 2-(5-methyl-2-phenyloxazol-4-yl)ethyl ester (3.74 g, 10.5 mmol), 3-(2-formyl-4-hydroxyphenyl)acrylic acid tert-butyl ester (2.0 g, 8.05 mmol), and anhydrous DMF (40 mL). Cesium carbonate (3.94 g, 12.1 mmol) was added, and the reaction was heated to 55° C. under a nitrogen atmosphere for 18 h. The volatiles were removed in vacuo, and the crude residue was dissolved in EtOAc (250 mL). The organic layer was washed with brine (2×), dried (Na2SO4), and concentrated to a yellow oil (1.70 g, 49%). 1H NMR (400 MHz, CDCl3) δ 1.54 (s, 9H), 2.38 (s, 3H), 3.01 (t, J=6.6 Hz, 2H), 4.34 (t, J=6.6 Hz, 2H), 6.24 (d, J=15.6 Hz, 1H), 7.12 (dd, J=8.8, 2.9 Hz, 1H), 7.38 (d, J=2.9 Hz, 1H), 7.40-7.45 (m, 3H), 7.58 (d, J=8.8 Hz, 1H), 7.98 (dd, J=6.4, 2.0 Hz, 2H), 8.33 (d, J=15.6 Hz, 1H), 10.3 (s, 1H). MS (ES) m/e 434 (M+1).

Workup

  1. customThe volatiles were removed in vacuo
  2. dissolutionthe crude residue was dissolved in EtOAc (250 mL)
  3. washThe organic layer was washed with brine (2×)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated to a yellow oil (1.70 g, 49%)

Sources & evidence

ORD record
ord-c47174a23b8c4f149bf792f3b2449544
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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