Water → Emakalim

HRID 275017Notes

Reaction equation

HRID 275017 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][C:8]([CH3:14])([CH3:13])[CH:7]1[O:15][CH:6]21)#[N:2].[OH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1.[OH-].C([N+](C)(C)C)C1C=CC=CC=1.O>O1CCOCC1>[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][C:8]([CH3:14])([CH3:13])[C@@H:7]([OH:15])[C@@H:6]2[N:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]1=[O:16])#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 66854Benzyltrimethylammonium hydroxideHCID 108673602,2-Dimethyl-3,4-epoxy-6-cyanochromanHCID 178516071HCID 178516071, compound

Product 1

HCID 9839143EmakalimYield 61.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1 g of 6-cyano-2,2-dimethyl-3,4-epoxychromane is refluxed for 40 hours with 1 g of 2-hydroxypyridine in 10 ml of dioxane, in the presence of 0.20 ml of a methanolic solution containing 35% of benzyltrimethylammonium hydroxide. The mixture is taken up with 30 ml of water and the precipitate obtained is filtered off, washed with isopropyl ether and then recrystallized from 20 ml of absolute ethyl alcohol to give 0.9 g of the expected product.

Workup

  1. customthe precipitate obtained
  2. filtrationis filtered off
  3. washwashed with isopropyl ether
  4. customrecrystallized from 20 ml of absolute ethyl alcohol

Sources & evidence

ORD record
ord-6a1322fc110a44d98c31dabbc5926f23
Source dataset
uspto-grants-1995_02
Patent number
US05391751

Reaction notes

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