Diisobutylaluminum hydride → HCID 86617997, compound

HRID 1869755Notes

Reaction equation

HRID 1869755 reaction equation
CC(C[AlH]CC(C)C)C.[F:10][C:11]([F:31])([F:30])[C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:13]=1[CH:22]([CH2:27][CH2:28][CH3:29])[C:23](OC)=[O:24].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>C1COCC1>[F:10][C:11]([F:30])([F:31])[C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:19])([F:20])[F:21])=[CH:14][C:13]=1[CH:22]([CH2:27][CH2:28][CH3:29])[CH2:23][OH:24]

Participants

5

Reactant 3

HCID 14487Diisobutylaluminum hydrideHCID 9855836Potassium sodium tartarateHCID 57987551HCID 57987551, compound

Product 1

HCID 86617997HCID 86617997, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DiBAL (7.62 ml, 1M in DCM, 7.62 mmol) was added to a solution of methyl 2-[2,5-bis(trifluoromethyl)phenyl]pentanoate (1 g, 3.05 mmol) in THF at −30° C. The mixture was stirred for 45 min. Sodium potassium tartrate (100 ml, satd. aq. solution) was added and the mixture was stirred at room temperature for 30 min then extracted into EtOAc. The combined organic phases were washed with brine, then dried (MgSO4) and concentrated in vacuo to give the product as a colourless oil. This was purified by chromatography on silica using hexane/EtOAc (9:1) as eluant to afford the product as an oil (710 mg). 1H NMR (500 MHz, CDCl3): δ 0.89 (3H, t, J 7.3), 1.10-1.20 (1H, m), 1.28-1.36 (1H, m), 1.60-1.68 (1H, m), 1.80-1.87 (1H, m), 3.33-3.39 (1H, m), 3.79 (2H, t, J 5.5), 7.59 (1H, d, J 8.3), 7.74 (1H, s), 7.79 (1H, d, J 8.2).

Workup

  1. stirringthe mixture was stirred at room temperature for 30 min
  2. extractionthen extracted into EtOAc
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5a4d92a739b24a27a2a40b20a7d1d1bc
Source dataset
uspto-grants-2009_12
Patent number
US07638629B2

Reaction notes

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