Diisobutylaluminum hydride → HCID 21935738, compound

HRID 1242448Notes

Reaction equation

HRID 1242448 reaction equation
[F:1][C:2]([F:24])([F:23])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[C:13]([C:20](Cl)=[O:21])=[CH:12][N:11]=2)=[CH:6][CH:5]=1.CC(C[AlH]CC(C)C)C.OS([O-])(=O)=O.[K+]>O1CCCC1>[F:24][C:2]([F:1])([F:23])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:15]=[C:14]([C:16]([F:17])([F:18])[F:19])[C:13]([CH2:20][OH:21])=[CH:12][N:11]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 14487Diisobutylaluminum hydrideHCID 516920Potassium bisulfateHCID 21935833HCID 21935833, compound

Product 1

HCID 21935738HCID 21935738, compoundYield 70.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.45 g (1.21 mmol) 2-(4-Trifluoromethoxy-phenyl)-4-trifluoromethyl-pyrimidine-5-carbonyl chloride in 4 ml tetrahydrofurane were cooled (-30° C.) and treated during 10 min with 2.23 ml (2.20 mmol) of a DIBALH-solution (1.2 M in toluene). The solution was allowed to come to 0° C. (1.5 h). The reaction was then powered to an ice-cooled aqueous 10% KHSO4 solution and extracted with ether. The ether-phase was washed with aqueous 10% NaCl solution, dried (NaSO4) and evaporated. The crude product was purified by flash chromatography over silica gel with heptane/AcOEt 9:1, to give 0.29 g of the title compound as an off-white solid.

Workup

  1. customto come to 0° C.
  2. custom(1.5 h)
  3. extractionextracted with ether
  4. washThe ether-phase was washed with aqueous 10% NaCl solution
  5. dry with materialdried (NaSO4)
  6. customevaporated
  7. customThe crude product was purified by flash chromatography over silica gel with heptane/AcOEt 9:1

Sources & evidence

ORD record
ord-12afb8dfb7e943659c061e63bb91bbe1
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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