Diisobutylaluminumhydride → 2-(Trifluoromethyl)pyrimidine-5-carbaldehyde

HRID 1047609Notes

Reaction equation

HRID 1047609 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.[H-].C([Al+]CC(C)C)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 21225700DiisobutylaluminumhydrideHCID 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 diisobutylaluminium hydride (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 hydrochloric acid (2.0 M). The mixture was allowed to warm to ambient temperature. The mixture was extracted with diethyl ether (3×). The combined organic extracts was dried over sodium sulfate, 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 hydrochloric acid (2.0 M)
  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 sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2032114121ad44bdb8426a84ed31d0ff
Source dataset
uspto-grants-2013_10
Patent number
US08569512B2

Reaction notes

Loading…