Diisobutylaluminum hydride → HCID 21935886, compound

HRID 1242335Notes

Reaction equation

HRID 1242335 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[N:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[CH:7][N:6]=1)=O.CC(C[AlH]CC(C)C)C>C1COCC1>[F:20][C:17]([F:18])([F:19])[C:14]1[CH:13]=[CH:12][C:11]([C:8]2[N:9]=[CH:10][C:5]([CH2:3][OH:2])=[N:6][CH:7]=2)=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 67072210HCID 67072210, compound

Product 1

HCID 21935886HCID 21935886, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.585 g (2.07 mmol) of the above synthesized 5-(4-trifluoromethyl-phenyl)-pyrazine-2-carboxylic acid methyl ester in 10 ml of abs. THF was cooled down to −30° C. and reacted with 5.18 ml of DIBAL-H-solution (1.2 M in toluene, 3 eq.) for 10 min. The reaction was warmed up during 2.5 h to 10° C. and stirred 1 h at RT. Careful quenching at 0° C. with saturated NaCl solution, twofold extraction with ether, washing with brine, drying over sodium sulfate, and evaporation of the solvents left a crude product which was purified by flash chromatography (SiO2, heptane/AcOEt=4/1) to deliver finally 0.325 g of the title compound as yellow solid.

Workup

  1. temperatureThe reaction was warmed up during 2.5 h to 10° C.
  2. customCareful quenching at 0° C. with saturated NaCl solution
  3. extractionextraction with ether
  4. washwashing with brine
  5. dry with materialdrying over sodium sulfate, and evaporation of the solvents
  6. waitleft a crude product which
  7. customwas purified by flash chromatography (SiO2, heptane/AcOEt=4/1)

Sources & evidence

ORD record
ord-8d5a65766a9f4c49b8cf29c4e6d02b3b
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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