Water → HCID 54733813, compound

HRID 1974836Notes

Reaction equation

HRID 1974836 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]=[C:21]([OH:23])[CH:20]=[CH:19][N:18]=1.[OH-].C([N+](C)(C)C)C1C=CC=CC=1.O>O1CCOCC1.CN(C)C=O>[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][C:21]([OH:23])=[CH:22][C:17]1=[O:16])#[N:2]

Participants

7

Reactant 4

HCID 962WaterHCID 66854Benzyltrimethylammonium hydroxideHCID 108673602,2-Dimethyl-3,4-epoxy-6-cyanochromanHCID 178516518HCID 178516518, compound

Product 1

HCID 54733813HCID 54733813, compoundYield 18.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

3 g of 6-cyano-2,2-dimethyl-3,4-epoxychromane are refluxed for 20 hours with 1.8 g of 2,4-dihydroxypyridine in 30 ml of dioxane and 20 ml of dimethylformamide, in the presence of 0.6 ml of a methanolic solution containing 35% of benzyltrimethylammonium hydroxide. The solvents are evaporated off under vacuum and the residue is then crystallized by the addition of isopropyl ether. The crystals obtained are taken up with water, filtered off and then washed with acetone to give 850 mg of the expected product.

Workup

  1. customThe solvents are evaporated off under vacuum
  2. customthe residue is then crystallized by the addition of isopropyl ether
  3. customThe crystals obtained
  4. filtrationfiltered off
  5. washwashed with acetone

Sources & evidence

ORD record
ord-419222a421b640a6935207e9085c9f77
Source dataset
uspto-grants-1994_02
Patent number
US05284838

Reaction notes

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