3,5-Heptanedione → HCID 22005256, compound

HRID 324891Notes

Reaction equation

HRID 324891 reaction equation
[CH3:1][C:2]([O:5][C:6]([CH2:8][C:9]([CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:10])=[O:7])([CH3:4])[CH3:3].[CH3:19][CH2:20][C:21](=O)[CH2:22][C:23](=O)[CH2:24][CH3:25].C[O-].[Na+]>CO>[CH2:20]([C:21]1[CH:22]=[C:23]([CH2:24][CH3:25])[C:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])=[C:9]([OH:10])[C:11]=1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH3:19]

Participants

5

Reactant 3

HCID 819233,5-HeptanedioneHCID 119788Bis(1,1-dimethylethyl) 3-oxoglutarateHCID 10942334Sodium Methoxide

Product 1

HCID 22005256HCID 22005256, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of di-tert-butyl 1,3-acetonedicarboxylate (10 g, 38.7 mmol), 3,5-heptanedione (6.5 g, 50.3 mmol) and sodium methoxide (2.7 g, 50.3 mmol) in methanol (100 mL) was stirred at room temperature overnight. Methanol was removed via rotary evaporation and the resulting orange sludge was partitioned between diethyl ether (100 mL) and 10% aqueous hydrochloric acid (100 mL). The separated aqueous layer was extracted with diethyl ether (50 mL×2). The combined organic portions were washed with saturated aqueous sodium chloride (20 mL), dried over sodium sulfate, filtered through a pad of silica (20 mm×40 mm) and concentrated in vacuo to yield a yellow oil (13.23 g, 97%): 1H NMR (300 MHz, CDCl3): δ 1.20 (t, 6H), 1.60 (s, 18H) 2.74 (q, 4H), 6.55 (s, 1H), 11.73 (s, 1H).

Workup

  1. customMethanol was removed via rotary evaporation
  2. customthe resulting orange sludge was partitioned between diethyl ether (100 mL) and 10% aqueous hydrochloric acid (100 mL)
  3. extractionThe separated aqueous layer was extracted with diethyl ether (50 mL×2)
  4. washThe combined organic portions were washed with saturated aqueous sodium chloride (20 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered through a pad of silica (20 mm×40 mm)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ae61b28b19e14a8ba073f2fd1cddf87a
Source dataset
uspto-grants-2001_04
Patent number
US06218431B1

Reaction notes

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