Diisobutylaluminumhydride → HCID 86681293, compound

HRID 2045957Notes

Reaction equation

HRID 2045957 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C[O:12][C:13]([C:15]1[O:16][C:17]([C:21]2[CH2:25][C:24]([C:30]3[CH:35]=[C:34]([Cl:36])[C:33]([Cl:37])=[C:32]([Cl:38])[CH:31]=3)([C:26]([F:29])([F:28])[F:27])[O:23][N:22]=2)=[CH:18][C:19]=1[CH3:20])=O>C(OCC)C.C(OCC)(=O)C>[CH3:20][C:19]1[CH:18]=[C:17]([C:21]2[CH2:25][C:24]([C:30]3[CH:31]=[C:32]([Cl:38])[C:33]([Cl:37])=[C:34]([Cl:36])[CH:35]=3)([C:26]([F:29])([F:28])[F:27])[O:23][N:22]=2)[O:16][C:15]=1[CH2:13][OH:12]

Participants

5

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 86681294HCID 86681294, compound

Product 1

HCID 86681293HCID 86681293, compoundYield 103.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

Diisobutylaluminium hydride (DIBAL-H, 12.1 ml, 1M in Toluene) is added to a solution of 3-methyl-5-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-furan-2-carboxylic acid methyl ester (1.84 g) in diethyl ether (30 ml) under nitrogen at −5° C. After 20 minutes at −5° C., the reaction mixture is diluted with ethyl acetate and is quenched with a saturated solution of NaHCO3. The resulted fine white precipitate is filtered and the aqueous phase is separated. The organic phase is washed with a saturated solution of NaHCO3 and with a saturated aqueous solution of NaCl, dried over MgSO4 and concentrated in vacuo. The crude product is purified on a semi-preparative HPLC to yield {3-methyl-5-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-furan-2-yl}-methanol (1.78 g) as a light yellow foam.

Workup

  1. customis quenched with a saturated solution of NaHCO3
  2. filtrationThe resulted fine white precipitate is filtered
  3. customthe aqueous phase is separated
  4. washThe organic phase is washed with a saturated solution of NaHCO3 and with a saturated aqueous solution of NaCl
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe crude product is purified on a semi-preparative HPLC

Sources & evidence

ORD record
ord-6c38c38fcd26432db51b797bcb78be9a
Source dataset
uspto-grants-2013_11
Patent number
US08592418B2

Reaction notes

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