Sodium Hydroxide → HCID 89586468, compound

HRID 1747760Notes

Reaction equation

HRID 1747760 reaction equation
[OH:1][CH:2]([C:4]1[C:5](=[O:23])[C:6]2[O:22][CH2:21][CH2:20][C:7]=2[N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[N:9]=1)[CH3:3].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH-].[Na+]>C(#N)C>[C:2]([C:4]1[C:5](=[O:23])[C:6]2[O:22][CH2:21][CH2:20][C:7]=2[N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[N:9]=1)(=[O:1])[CH3:3]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 89586288HCID 89586288, compound

Product 1

HCID 89586468HCID 89586468, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-(1-hydroxyethyl)-1-[3-(trifluoromethyl)phenyl]-6,7-dihydrofuro[3,2-c]pyridazin-4(1H)-one (0.858 g) in acetonitrile (20 mL) was added Dess-Martin Periodinane (1.23 g) portionwise, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into 1M aqueous sodium hydroxide solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/methanol) and recrystallized from ethyl acetate to give the title compound (0.739 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/methanol)
  6. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-d8c81fc78e3443a1a996827d1e713b31
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Reaction notes

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