Sodium Hydroxide → HCID 14742805, compound

HRID 1651275Notes

Reaction equation

HRID 1651275 reaction equation
C[O:2][C:3](=[O:23])/[CH:4]=[CH:5]/[C:6]1[N:7]([CH3:22])[C:8]2[C:13]([C:14]=1[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:12][CH:11]=[C:10]([O:20][CH3:21])[CH:9]=2.[OH-].[Na+]>CO>[CH3:21][O:20][C:10]1[CH:9]=[C:8]2[C:13]([C:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[C:6](/[CH:5]=[CH:4]/[C:3]([OH:23])=[O:2])[N:7]2[CH3:22])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14742793HCID 14742793, compound

Product 1

HCID 14742805HCID 14742805, compoundYield 47.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

As in Example 112, (E)-3-(6-methoxy-1-methyl-3-pentylindol-2-yl)-2-propenoic acid methyl ester (2 g) in methanol (25 mL) was treated with 4N sodium hydroxide solution (3 mL) at reflux for 2.5 hours. The crude reaction product was isolated in the usual manner giving 0.91 g of (E)-3-(6-methoxy-1-methyl-3-pentylindol-2-yl)-2-propenoic acid. A small sample was crystallized from diethyl ether to give the analytical specimen, mp 157°-158° C. Anal. Calcd for C18H23NO3 : C, 71.73; H, 7.69; N, 4.65 Found: C, 72.06; H, 7.65; N, 4.82

Workup

  1. temperatureat reflux for 2.5 hours
  2. customThe crude reaction product
  3. customwas isolated in the usual manner

Sources & evidence

ORD record
ord-30a7f62063fa4052bc95c669988cabf8
Source dataset
uspto-grants-1990_05
Patent number
US04927838

Reaction notes

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