Diisobutylaluminumhydride → {2-Methyl-5-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-furan-3-yl}-methanol

HRID 68577Notes

Reaction equation

HRID 68577 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C[O:12][C:13]([C:15]1[CH:19]=[C:18]([C:20]2[CH2:24][C:23]([C:29]3[CH:34]=[C:33]([Cl:35])[C:32]([Cl:36])=[C:31]([Cl:37])[CH:30]=3)([C:25]([F:28])([F:27])[F:26])[O:22][N:21]=2)[O:17][C:16]=1[CH3:38])=O>C(OCC)C>[CH3:38][C:16]1[O:17][C:18]([C:20]2[CH2:24][C:23]([C:29]3[CH:34]=[C:33]([Cl:35])[C:32]([Cl:36])=[C:31]([Cl:37])[CH:30]=3)([C:25]([F:27])([F:26])[F:28])[O:22][N:21]=2)=[CH:19][C:15]=1[CH2:13][OH:12]

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 867066522-Methyl-5-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-furan-3-carboxylic acid methyl ester

Product 1

HCID 86706651{2-Methyl-5-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-furan-3-yl}-methanolYield 82.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Diisobutylaluminium hydride (DIBAL-H, 21.9 ml, 1M in toluene) is added to a solution of 2-methyl-5-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-furan-3-carboxylic acid methyl ester (5.0 g) in diethyl ether (100 ml) under nitrogen at −5° C. After 15 it at −5° C., the cold bad is removed. After 20 hours at room temperature, the reaction mixture is diluted with ethyl acetate and is quenched with a saturated solution of NaHCO3. The organic phase is separated and washed with a saturated solution of NaHCO3 and with a saturated aqueous solution of NaCl, dried over Na2SO4 and concentrated in vacuo. The crude product is purified on a semi-preparative HPLC to yield {2-methyl-5-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-furan-3-yl}-methanol (3.88 g) as a white foam. MS (HPLC/MS): 428 (MH+).

Workup

  1. customAfter 15 it at −5° C., the cold bad is removed
  2. additionthe reaction mixture is diluted with ethyl acetate
  3. customis quenched with a saturated solution of NaHCO3
  4. customThe organic phase is separated
  5. washwashed with a saturated solution of NaHCO3 and with a saturated aqueous solution of NaCl
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe crude product is purified on a semi-preparative HPLC

Sources & evidence

ORD record
ord-640e62c587444dcda9038f5d6d349d83
Source dataset
uspto-grants-2014_09
Patent number
US08822466B2

Reaction notes

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