Benzyltrimethylammonium hydroxide → HCID 14476368, compound

HRID 1974835Notes

Reaction equation

HRID 1974835 reaction equation
[CH3:1][C:2]1([CH3:19])[CH:11]2[O:12][CH:10]2[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])[CH:8]=2)[O:3]1.[OH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1.[OH-].C([N+](C)(C)C)C1C=CC=CC=1>O1CCOCC1>[O:20]=[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]1[C@@H:10]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])[CH:8]=2)[O:3][C:2]([CH3:19])([CH3:1])[C@H:11]1[OH:12]

Participants

5

Reactant 3

HCID 66854Benzyltrimethylammonium hydroxideHCID 14476366HCID 14476366, compoundHCID 178516071HCID 178516071, compound

Product 1

HCID 14476368HCID 14476368, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture containing 1.9 g of 2,2-dimethyl-3,4-epoxy-6-trifluoroacetylchromane (PREPARATION II), 1.4 g of 2-hydroxypyridine, 5 ml of dioxane and 0.2 ml of a methanolic solution containing 35% of benzyltrimethylammonium hydroxide is refluxed for 20 hours. The residue obtained after concentration under vacuum is taken up with 20 ml of water and the insoluble material is then filtered off and washed with water and boiling isopropyl ether. It is chromatographed on a column of 50 g of silica using a methylene chloride/ethyl acetate mixture (7/3) as the eluent. This gives 0.3 g of dry product.

Workup

  1. temperatureis refluxed for 20 hours
  2. customThe residue obtained
  3. concentrationafter concentration under vacuum
  4. filtrationthe insoluble material is then filtered off
  5. washwashed with water
  6. customIt is chromatographed on a column of 50 g of silica using a methylene chloride/ethyl acetate mixture (7/3) as the eluent

Sources & evidence

ORD record
ord-6730829e97224e6d8a4055a09030ba97
Source dataset
uspto-grants-1994_02
Patent number
US05284838

Reaction notes

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