Ethyl orthoformate → alpha-Carbethoxy-alpha-diethoxymethyl-beta-(3,4,5-trimethoxyphenyl)propionitrile

HRID 614281Notes

Reaction equation

HRID 614281 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].[CH:22](OCC)([O:26][CH2:27][CH3:28])[O:23][CH2:24][CH3:25]>>[C:8]([C:7]([CH:22]([O:26][CH2:27][CH3:28])[O:23][CH2:24][CH3:25])([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 31214Ethyl orthoformateHCID 11277800HCID 11277800, compound

Product 1

HCID 12559126alpha-Carbethoxy-alpha-diethoxymethyl-beta-(3,4,5-trimethoxyphenyl)propionitrileYield 82%

Procedure

A solution of ethyl 3,4,5-trimethoxybenzylcyanoacetate (14.7g) in triethyl orthoformate (100 ml) was heated at reflux for 18 hours using a steam-jacketed column for continuous removal of ethanol. The solution was cooled, and most of the excess orthoformate was removed in vacuo. The crystals obtained were washed with ether and dried to yield colourless crystals of α-carbethoxy-α-diethoxymethyl-β-(3,4,5-trimethoxy phenyl)propionitrile (16.3 g, 82%), m.p. 91θ ; nmr (CDCl3) δ1.13, 1.20. and 1.32 (triplets, 9, CH3CH2O-), 3.15 (s, 2, Ar-CH2 -C), 3.4-4.0 (m, 4, m, 4, CH3CH2 -O), 3.85 (s, 9, -C6H2 -(OCH3)3), 4.13 (q, 2, CH3CH2 -OCO), 4.80 (s, 1, -CH (OEt)2), and 6.55 (s, 2, aromatic H). Anal. Calcd. for C20H29NO7 : C, 60.74; H, 7.39; N, 3.54. Found: C, 60.56; H, 7.33; N, 3.64.

Workup

  1. temperatureat reflux for 18 hours
  2. customfor continuous removal of ethanol
  3. temperatureThe solution was cooled
  4. custommost of the excess orthoformate was removed in vacuo
  5. customThe crystals obtained
  6. washwere washed with ether
  7. customdried

Sources & evidence

ORD record
ord-0df57b12c20748ae8feef2ce8512fb1b
Source dataset
uspto-grants-1979_03
Patent number
US04144263

Reaction notes

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