Benzyltrimethylammonium hydroxide → trans-6-Cyano-4-(1,2-dihydro-4-fluoro-2-oxopyrid-1-yl)-2,2-dimethylchroman-3-ol

HRID 1974840Notes

Reaction equation

HRID 1974840 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].[F:16][C:17]1[CH:22]=[CH:21][NH:20][C:19](=[O:23])[CH:18]=1.[OH-].C([N+](C)(C)C)C1C=CC=CC=1>O1CCCC1>[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:20]1[CH:21]=[CH:22][C:17]([F:16])=[CH:18][C:19]1=[O:23])#[N:2]

Participants

5

Reactant 3

HCID 66854Benzyltrimethylammonium hydroxideHCID 3384594-Fluoropyridin-2-olHCID 108673602,2-Dimethyl-3,4-epoxy-6-cyanochroman

Product 1

HCID 67823918trans-6-Cyano-4-(1,2-dihydro-4-fluoro-2-oxopyrid-1-yl)-2,2-dimethylchroman-3-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture containing 460 mg of 6-cyano-2,2-dimethyl-3,4-epoxychromane, 283 mg of 4-fluoropyrid-2-one (PREPARATION III) and 0.05 ml of a methanolic solution containing 35% of benzyltrimethylammonium hydroxide, in 5 ml of tetrahydrofuran, is refluxed for 24 hours. The solvent is concentrated, the residue is taken up in ethyl acetate and the organic phase is then washed with water, dried over sodium sulfate and concentrated under vacuum. The residue obtained is chromatographed on silica using a methylene chloride/methanol mixture (97/3) as the eluent. 200 ml of a white solid are recovered.

Workup

  1. concentrationThe solvent is concentrated
  2. washthe organic phase is then washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe residue obtained
  6. customis chromatographed on silica using a methylene chloride/methanol mixture (97/3) as the eluent
  7. custom200 ml of a white solid are recovered

Sources & evidence

ORD record
ord-1ffec3daa4f24dde9dcea24d74249c9a
Source dataset
uspto-grants-1994_02
Patent number
US05284838

Reaction notes

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