Ethyl orthoformate → HCID 70587138, compound

HRID 1855804Notes

Reaction equation

HRID 1855804 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(OCC)(OCC)O[CH2:24][CH3:25]>>[CH2:11]([O:10][CH:8]([CH:7]([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:9][CH2:24][CH3:25])[CH3:12]

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 11277800HCID 11277800, compound

Product 1

HCID 70587138HCID 70587138, compoundYield 82%

Procedure

A solution of ethyl 3,4,5-trimethoxybenzylcyanoacetate (14.7 g) in triethyl orthoformate (100 ml) has 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-of diethoxymethyl-β-(3,4,5-trimethoxy phenyl)propionitrile (16.3 g, 82%), m.p. 91°; 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-374b99f360fa4c87babe027f03ae2fd9
Source dataset
uspto-grants-1980_08
Patent number
US04216319

Reaction notes

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