Triacetoxyperiodinane → HCID 178519624, compound

HRID 1424409Notes

Reaction equation

HRID 1424409 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:24])[C:9]2[N:18]=[C:17]([OH:19])[C:16]3[C:11](=[CH:12][C:13]([C:20]([F:23])([F:22])[F:21])=[CH:14][CH:15]=3)[N:10]=2)=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)(O)[O-].[Na+]>C(#N)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:9]2[N:18]=[C:17]([OH:19])[C:16]3[C:11](=[CH:12][C:13]([C:20]([F:22])([F:21])[F:23])=[CH:14][CH:15]=3)[N:10]=2)=[O:24])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 178517843HCID 178517843, compound

Product 1

HCID 178519624HCID 178519624, compoundYield 129.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 2-((4-fluorophenyl)(hydroxy)methyl)-7-(trifluoromethyl)quinazolin-4-ol (2000 mg, 5.89 mmol) was added Dess-Martin periodinane (3000 mg, 7.07 mmol) in acetonitrile (25 mL) and the mixture was stirred at rt for 2 h. To the crude mixture was added aq sodium bicarbonate solution and the mixture was stirred for 0.5 h. The resulting brown precipitate was collected, washed with diethyl ether and dried under high vacuum to afford (4-fluorophenyl)(4-hydroxy-7-(trifluoromethyl)quinazolin-2-yl)methanone (2.57 g, quantitative yield) LC-MS (ESI) m/z 336 (M+Na)+.

Workup

  1. stirringthe mixture was stirred for 0.5 h
  2. customThe resulting brown precipitate was collected
  3. washwashed with diethyl ether
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-978e43a1c84845d2b35ba6175dabdadd
Source dataset
uspto-grants-2015_01
Patent number
US08927711B2

Reaction notes

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