Diisobutylaluminumhydride → 2-[5-(4-Chlorophenyl)-2-(trifluoromethyl)-3-furyl]ethanol

HRID 9661Notes

Reaction equation

HRID 9661 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C[O:12][C:13](=O)[CH2:14][C:15]1[CH:19]=[C:18]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)[O:17][C:16]=1[C:27]([F:30])([F:29])[F:28]>C1(C)C=CC=CC=1.O1CCCC1>[Cl:26][C:23]1[CH:22]=[CH:21][C:20]([C:18]2[O:17][C:16]([C:27]([F:28])([F:29])[F:30])=[C:15]([CH2:14][CH2:13][OH:12])[CH:19]=2)=[CH:25][CH:24]=1

Participants

5

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 21986299Methyl[5-(4-chlorophenyl)-2-(trifluoromethyl)-3-furyl]acetate2×

Product 1

HCID 219864132-[5-(4-Chlorophenyl)-2-(trifluoromethyl)-3-furyl]ethanol

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.5 M Diisobutylaluminium hydride in toluene (0.8 ml) was added to a solution of methyl[5-(4-chlorophenyl)-2-(trifluoromethyl)-3-furyl]acetate (intermediate 86, 0.10 g) in tetrahydrofuran (5 ml) at 0° C. under nitrogen. The solution was allowed to stir thus for 2.5 hours then was quenched with methanol and allowed to warm to room temperature. Silica was added and the solvent was removed in vacuo. The crude product was purified using SPE (silica cartridge): the product was eluted using cyclohexane:ethyl acetate (5:1) and concentrated to form a colourless oil.

Workup

  1. customthen was quenched with methanol
  2. additionSilica was added
  3. customthe solvent was removed in vacuo
  4. customThe crude product was purified
  5. washthe product was eluted
  6. concentrationconcentrated
  7. customto form a colourless oil

Sources & evidence

ORD record
ord-35fbf77d81c9458bb2baceb830e52f52
Source dataset
uspto-grants-2006_08
Patent number
US07091237B2

Reaction notes

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