3-Methylbutanal → HCID 69562212, compound

HRID 2298996Notes

Reaction equation

HRID 2298996 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]2[CH:25]=[C:24]3[C:19]([CH2:20][CH2:21][N:22]=[C:23]3[CH:26]([CH3:28])[CH3:27])=[CH:18][CH:17]=2)[CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([C:12]#[N:13])[CH:8]=[CH:7]2.C([Li])CCC.[CH:34](=[O:39])[CH2:35][CH:36]([CH3:38])[CH3:37]>C1COCC1>[OH:39][CH:34]([C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]2[CH:25]=[C:24]3[C:19]([CH2:20][CH2:21][N:22]=[C:23]3[CH:26]([CH3:28])[CH3:27])=[CH:18][CH:17]=2)[CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([C:12]#[N:13])[CH:8]=[CH:7]2)[CH2:35][CH:36]([CH3:38])[CH3:37]

Participants

5

Reactant 3

HCID 115523-MethylbutanalHCID 69561723HCID 69561723, compoundHCID 178418339Butyllithium

Product 1

HCID 69562212HCID 69562212, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of Example 8E (250 mg, 0.52 mmol) in THF (5 mL) at −90° C. was treated with 2.5M n-butyllithium in hexanes (0.210 mL, 0.525 mmol), stirred for 2 minutes, treated with isovaleraldehyde (0.056 mL, 0.63 mmol), and stirred for 30 minutes. The reaction was warmed to room temperature, quenched with water, and extracted with ethyl acetate. The combined extracts were dried (Na2SO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 25% ethyl acetate/hexanes to provide the desired product.

Workup

  1. stirringstirred for 30 minutes
  2. customquenched with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was purified by flash column chromatography on silica gel with 25% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-da2594876b83443ea8d752bb123a9bf3
Source dataset
uspto-grants-2002_12
Patent number
US06495562B1

Reaction notes

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