Methanol → (5-Cyclopropyl-3-(2,6-dichlorophenyl)isoxazol-4-yl)methanol

HRID 1689801Notes

Reaction equation

HRID 1689801 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.C[O:19][C:20]([C:22]1[C:23]([C:30]2[C:35]([Cl:36])=[CH:34][CH:33]=[CH:32][C:31]=2[Cl:37])=[N:24][O:25][C:26]=1[CH:27]1[CH2:29][CH2:28]1)=O.CO>C1COCC1.CCOC(C)=O.O>[CH:27]1([C:26]2[O:25][N:24]=[C:23]([C:30]3[C:31]([Cl:37])=[CH:32][CH:33]=[CH:34][C:35]=3[Cl:36])[C:22]=2[CH2:20][OH:19])[CH2:29][CH2:28]1

Participants

8

Reactant 4

HCID 887MethanolHCID 1140TolueneHCID 21225700DiisobutylaluminumhydrideHCID 53421832Methyl 5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazole-4-carboxylate

Product 1

HCID 45790382(5-Cyclopropyl-3-(2,6-dichlorophenyl)isoxazol-4-yl)methanolYield 85.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Diisobutylaluminium hydride 1M/toluene (4.62 L, 4.62 mol) is added dropwise to a stirred solution of 5-Cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazole-4-carboxylic acid methyl ester (687.14 g, 2.20 mol) in THF (4.4 L) at 0° C. The reaction is stirred at room temperature for 2 hours. Methanol (150 mL) is added over the mixture at 0° C. and stirred for 10 min. Then, water (2.2 L) and EtOAc (4.3 L) is added. The precipitate formed is filtered through celite and all the solvents are removed in vacuum. The solid is triturated in 1 L of hexane and dried under vacuum filtration to obtain title compound (534.7 g, 85% yield) as a white solid. MS (m/e): 312 (M+1).

Workup

  1. stirringstirred for 10 min
  2. customThe precipitate formed
  3. filtrationis filtered through celite and all the solvents
  4. customare removed in vacuum
  5. customThe solid is triturated in 1 L of hexane
  6. customdried under vacuum filtration

Sources & evidence

ORD record
ord-6861bdfa0f9040e58431e71ada8b07bc
Source dataset
uspto-grants-2012_04
Patent number
US08153624B2

Reaction notes

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