Sulfuric acid magnesium salt (1:1) → 3-Butyl-5-methyl-isoxazole-4-carbaldehyde

HRID 1923605Notes

Reaction equation

HRID 1923605 reaction equation
C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.S([O-])([O-])(=O)=O.[Mg+2].[CH2:18]([C:22]1[C:26]([CH2:27][OH:28])=[C:25]([CH3:29])[O:24][N:23]=1)[CH2:19][CH2:20][CH3:21]>C(Cl)Cl.CCOCC>[CH2:18]([C:22]1[C:26]([CH:27]=[O:28])=[C:25]([CH3:29])[O:24][N:23]=1)[CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 66599297(3-Butyl-5-methyl-isoxazol-4-yl)-methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 866443693-Butyl-5-methyl-isoxazole-4-carbaldehydeYield 85.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of PCC (4.96 g, 23 mmol) and anhydrous magnesium sulfate (7.40 g, 61 mmol) in DCM (60 mL) was added a solution of (3-butyl-5-methyl-isoxazol-4-yl)-methanol (2.6 g, 15 mmol) in DCM (60 mL) at room temperature and under argon. After 3 h the reaction mixture was diluted with ether (100 mL) and filtered through a bed of silica. The filtrate was concentrated in vacuo and purified by chromatography (silica, 0 to 50% ethyl acetate in heptane) to give the title compound (2.15 g, 84%) as a colourless liquid. MS: m/e=168.0 [M+H]+.

Workup

  1. filtrationfiltered through a bed of silica
  2. concentrationThe filtrate was concentrated in vacuo
  3. custompurified by chromatography (silica, 0 to 50% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-c0949176269e45858e62bbb8d535b132
Source dataset
uspto-grants-2012_05
Patent number
US08178522B2

Reaction notes

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