Diisobutylaluminum hydride → 2-(Trifluoromethyl)pyrimidine-5-carbaldehyde

HRID 1909117Notes

Reaction equation

HRID 1909117 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[N:8]=[CH:7][C:6]([C:9](OCC)=[O:10])=[CH:5][N:4]=1.CC(C[AlH]CC(C)C)C>ClCCl>[F:15][C:2]([F:1])([F:14])[C:3]1[N:4]=[CH:5][C:6]([CH:9]=[O:10])=[CH:7][N:8]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 21936133Ethyl 2-(trifluoromethyl)pyrimidine-5-carboxylate

Product 1

HCID 177509412-(Trifluoromethyl)pyrimidine-5-carbaldehydeYield 138.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of ethyl 2-(trifluoromethyl)pyrimidine-5-carboxylate (25.5 g, 116.0 mmol) in dichloromethane (580 mL) at −78° C. was slowly added DIBAL-H (1.0 M; 130.0 mL, 130.0 mmol). The mixture was stirred at −78° C. After 2 h, the mixture was quenched via slow addition of HCl (2.0 M in water). The mixture was allowed to warm to ambient temperature. The mixture was extracted with diethyl ether (3×). The combined organic extracts was dried over Na2SO4, filtered and concentrated to give the title compound (28.2 g).

Workup

  1. customat −78° C.
  2. customthe mixture was quenched via slow addition of HCl (2.0 M in water)
  3. temperatureto warm to ambient temperature
  4. extractionThe mixture was extracted with diethyl ether (3×)
  5. dry with materialThe combined organic extracts was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-de13c4656c45496db93bd3cdc0c20ca8
Source dataset
uspto-grants-2013_12
Patent number
US08598209B2

Reaction notes

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