Triacetoxyperiodinane → 4-Chloroquinazoline-6-carbaldehyde

HRID 2261085Notes

Reaction equation

HRID 2261085 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][OH:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:12]=[O:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 57469640(4-Chloroquinazolin-6-yl)methanol

Product 1

HCID 574696394-Chloroquinazoline-6-carbaldehydeYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-chloroquinazoline-6-yl-methanol (3.5 g, 0.018 mol) in dry CH2Cl2 (100 mL) was added Dess-Martin periodinane (8.4 g, 0.019 mol) and stirred at RT for 30 min. The reaction mixture was washed with 10% aqueous NaHCO3 (75 mL), water, brine and dried. The solvent was removed under vacuum to give 4-chloroquinazoline-6-carboxaldehyde (3 g, 88%) as pale yellow solid.

Workup

  1. washThe reaction mixture was washed with 10% aqueous NaHCO3 (75 mL), water, brine
  2. customdried
  3. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-3bbf0f5ef22440dab9146ef51f7f2986
Source dataset
uspto-grants-2010_12
Patent number
US07846925B2

Reaction notes

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