Methanol, 1,1-diethoxy-, 1-acetate → alpha-Carbethoxy-alpha-diethoxymethyl-beta-(3,4,5-trimethoxyphenyl)propionitrile

HRID 614284Notes

Reaction equation

HRID 614284 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[C:16]([O:20][CH3:21])[C:17]=1[O:18][CH3:19])[CH2:6][CH:7]([C:13]#[N:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9].[C:22]([O:25][CH:26](OCC)[O:27][CH2:28][CH3:29])(=O)[CH3:23]>>[C:8]([C:7]([CH:26]([O:27][CH2:28][CH3:29])[O:25][CH2:22][CH3:23])([CH2:6][C:5]1[CH:15]=[C:16]([O:20][CH3:21])[C:17]([O:18][CH3:19])=[C:3]([O:2][CH3:1])[CH:4]=1)[C:13]#[N:14])([O:10][CH2:11][CH3:12])=[O:9]

Participants

3

Reactant 2

HCID 84166Methanol, 1,1-diethoxy-, 1-acetateHCID 11277800HCID 11277800, compound

Product 1

HCID 12559126alpha-Carbethoxy-alpha-diethoxymethyl-beta-(3,4,5-trimethoxyphenyl)propionitrileYield 73%

Conditions

Temperature
95 °C

Procedure

Ethyl 3,4,5-trimethoxybenzylcyanoacetate (5 g) was mixed with diethoxymethyl acetate (15 g) and heated at 95° C. overnight. The mixture was cooled and crystallized by addition of ether-hexane (1:1, 25 ml). The product was filtered and dried under reduced pressure giving 4.9 g (73%) of white solid, m.p. 95°-97° C.

Workup

  1. temperatureThe mixture was cooled
  2. customcrystallized by addition of ether-hexane (1:1, 25 ml)
  3. filtrationThe product was filtered
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-4bcba33e5cd2494c8020951e6fe151bb
Source dataset
uspto-grants-1979_03
Patent number
US04144263

Reaction notes

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