3-Methylbutanal → HCID 59487403, compound

HRID 1099586Notes

Reaction equation

HRID 1099586 reaction equation
O=[C:2]([CH2:8][CH3:9])[CH2:3][C:4]([O:6][CH3:7])=[O:5].CC1(C)O[C:15](=[O:17])[CH2:14][C:13](=O)O1.C([O-])(=O)C.[NH4+:24].[CH3:25][CH:26]([CH3:30])[CH2:27]C=O>C(O)(=O)C>[CH2:8]([C:2]1[NH:24][C:15](=[O:17])[CH2:14][CH:13]([CH2:25][CH:26]([CH3:30])[CH3:27])[C:3]=1[C:4]([O:6][CH3:7])=[O:5])[CH3:9]

Participants

6

Reactant 4

HCID 115523-MethylbutanalHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 121699Methyl 3-oxovalerateHCID 517165Ammonium Acetate

Product 1

HCID 59487403HCID 59487403, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

500 mg (5.81 mmol) of methyl 3-oxopentanoate, 755 mg (5.81 mmol) of 2,2-dimethyl-1,3-dioxane-4,6-dione and 492 mg (6.39 mmol) of ammonium acetate were initially charged in 5 ml of acetic acid, and 0.623 ml (5.81 mmol) of 3-methylbutyraldehyde was added. The mixture was then stirred for 14 h each at room temperature and at 130° C. After removal of the volatile components on a rotary evaporator, the residue was purified by preparative HPLC (mobile phase: acetonitrile/water with 0.1% formic acid, gradient 20:80→95:5). Drying under high vacuum gave 390 mg (28% of theory) of the target compound.

Workup

  1. customat 130° C
  2. customAfter removal of the volatile components
  3. customon a rotary evaporator
  4. customthe residue was purified by preparative HPLC (mobile phase: acetonitrile/water with 0.1% formic acid, gradient 20:80→95:5)
  5. customDrying under high vacuum
  6. customgave 390 mg (28% of theory) of the target compound

Sources & evidence

ORD record
ord-8ac3c55181ab46a1b808c4eaa7d35042
Source dataset
uspto-grants-2012_03
Patent number
US08143411B2

Reaction notes

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