Methyl Acrylate → HCID 54057636, compound

HRID 1266463Notes

Reaction equation

HRID 1266463 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][C:7]([CH:8]=[N:9][CH2:10][Si](C)(C)C)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[C:26]([O:30][CH3:31])(=[O:29])[CH:27]=[CH2:28]>O1CCCC1>[CH3:31][O:30][C:26]([CH:27]1[CH2:28][CH2:10][N:9]([C:17](=[O:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:8]1[C:7]1[CH:15]=[CH:16][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)=[O:29]

Participants

5

Reactant 3

HCID 7294Methyl AcrylateHCID 7412Benzoyl chlorideHCID 53803212HCID 53803212, compound

Product 1

HCID 54057636HCID 54057636, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
45 °C

Procedure

A stirred solution of (4-nitro-benzylidene)-trimethylsilanylmethyl-amine (22 g, prepared as described in Chem. Pharm. Bull. 31(11) page 3939, 1893) in tetrahydrofuran (440 ml), at 45° C., was treated dropwise over 1.5 hour with a mixture of benzoyl chloride (10.1 ml) and methyl acrylate (9.3 ml) in tetrahydrofuran (500 ml). After stirring for 2.5 hours at 45° C. the mixture was allowed to cool to 20° C. then evaporated (40° C. and 2.7 kPa). The residue was dissolved in ethyl acetate (800 ml) and the solution was washed with hydrochloric acid (500 ml, 1N), then with aqueous sodium hydroxide solution (500 ml, 1N), then with water (500 ml), then dried over magnesium sulphate and then evaporated (40° C. and 2.7 kPa). The residue was subjected to chromatography on silica (500 g, 0.020-0.045 mm particle size) using a 60 mm internal diameter column and eluting with a mixture of cyclohexane and ethyl acetate (80:20, v/v) at 100 ml/minute affording the title compound (8.33 g) as a yellowish powder. 1H-NMR [500 MHz, (CD3)2SO at 373° K.] δ 2.19 (m, 1H); 2.32 (m, 1H); 3.34 (s, 3H); 3.70 (m, 2H); 4.03 (m, 1H); 5.52 (m, 1H); 7.35 to 7.50 (m, 7H); 8.12 (d, J=8.5 Hz, 2H). MS (EI): 354[M]+.

Workup

  1. temperatureto cool to 20° C.
  2. customthen evaporated (40° C. and 2.7 kPa)
  3. dissolutionThe residue was dissolved in ethyl acetate (800 ml)
  4. washthe solution was washed with hydrochloric acid (500 ml, 1N)
  5. dry with materialwith aqueous sodium hydroxide solution (500 ml, 1N), then with water (500 ml), then dried over magnesium sulphate
  6. customevaporated (40° C. and 2.7 kPa)
  7. washeluting with a mixture of cyclohexane and ethyl acetate (80:20, v/v) at 100 ml/minute

Sources & evidence

ORD record
ord-d70154262d5c416e855af591b61d82ea
Source dataset
uspto-grants-2003_04
Patent number
US06548533B2

Reaction notes

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