Sodium hydride → (E)-3-Phenylacrylic acid 4-{methoxycarbonylmethyl-[(E)-(3-phenylacryloyl)]-amino}phenyl ester

HRID 655185Notes

Reaction equation

HRID 655185 reaction equation
[H-].[Na+].[C:3]1(/[CH:9]=[CH:10]/[C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21](=[O:30])/[CH:22]=[CH:23]/[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:16][CH:15]=2)=[O:12])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:32][C:33]([O:35][CH3:36])=[O:34]>C1COCC1.C(OCC)(=O)C>[CH3:36][O:35][C:33]([CH2:32][N:13]([C:11](=[O:12])/[CH:10]=[CH:9]/[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)[C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21](=[O:30])/[CH:22]=[CH:23]/[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[CH:16][CH:15]=1)=[O:34]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 12345024-(Cinnamoylamino)phenyl 3-phenylacrylate

Product 1

HCID 59212038(E)-3-Phenylacrylic acid 4-{methoxycarbonylmethyl-[(E)-(3-phenylacryloyl)]-amino}phenyl esterYield 61.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (60%, 162 mg, 4.06 mmol) was washed with anhydrous THF (×2) and then suspended in anhydrous THF (20 mL). To this was added (E)-3-phenylacrylic acid 4-[(E)-(3-phenylacryloyl)amino]phenyl ester 11 (1.00 g, 2.71 mmol) followed by methyl bromoacetate (0.51 mL, 5.41 mmol). The reaction mixture was stirred at room temperature for 3 days. It was then diluted with ethyl acetate and washed with brine (×3), dried (Na2SO4) and evaporated. The resultant residue was purified by flash column chromatography on silica gel, eluting with petrol/ethyl acetate (2:1→1:1) and then ethyl acetate, to afford the title compound (0.734 g, 61%). 1HNMR (300 MHz) (CDCl3) δ 3.77 (3H, s), 4.52 (2H, s), 6.43 (1H, d, J=16 Hz), 6.65 (1H, d, J=16 Hz), 7.25-7.40 (7H, m), 7.45 (4H, m), 7.61 (3H, m), 7.75 (1H, d, J=16 Hz) and 7.91 (1H, d, J=16 Hz).

Workup

  1. washwashed with brine (×3)
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customThe resultant residue was purified by flash column chromatography on silica gel
  5. washeluting with petrol/ethyl acetate (2:1→1:1)

Sources & evidence

ORD record
ord-e9c3f53cb9b34958a31a18fc0dbdcef1
Source dataset
uspto-grants-2011_12
Patent number
US08071582B2

Reaction notes

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