Pyruvic Acid → HCID 89601336, compound

HRID 523346Notes

Reaction equation

HRID 523346 reaction equation
[O:1]=[C:2]([CH3:6])[C:3]([OH:5])=[O:4].[CH3:7]/[C:8](/[CH2:12][CH2:13][CH:14]=[C:15]([CH3:17])[CH3:16])=[CH:9]\[CH2:10]O.C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.ClCCl>[O:1]=[C:2]([CH3:6])[C:3]([O:5][CH2:10]/[CH:9]=[C:8](\[CH3:7])/[CH2:12][CH2:13][CH:14]=[C:15]([CH3:17])[CH3:16])=[O:4]

Participants

6

Reactant 3

HCID 1060Pyruvic AcidHCID 10868DicyclohexylcarbodiimideHCID 637566Geraniol

Product 1

HCID 89601336HCID 89601336, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 2-oxopropanoic acid (3.40 g, 38.6 mmol), DMAP (0.48 g, 3.9 mmol) and (E)-3,7-dimethyl-2,6-octadienol (10.00 g, 64.8 mmol) in dichloromethane (90 ml) was cooled on an ice-bath before a solution of DCC (9.18 g, 44.5 mmol) in dichloromethane (45 ml) was added during 30 min. The reaction mixture was stirred for 10 min at 0° C., then at room temperature for ca. 5 h. The precipitate formed in the reaction was filtered off and the filtrate taken up in ether, washed with water (3×), HCl (10%, 3×), a saturated solution of NaHCO3 (3×) and water. The organic layer was dried (Na2SO4) and concentrated. Column chromatography (SiO2, heptane/ether 4:1) gave 4.68 g (53%) of a slightly yellow oil.

Workup

  1. additionwas added during 30 min
  2. waitat room temperature for ca. 5 h
  3. customThe precipitate formed in the reaction
  4. filtrationwas filtered off
  5. washwashed with water (3×), HCl (10%, 3×)
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. concentrationconcentrated
  8. customColumn chromatography (SiO2, heptane/ether 4:1) gave 4.68 g (53%) of a slightly yellow oil

Sources & evidence

ORD record
ord-a3c5cc91aa42403695c48ff1493a66cd
Source dataset
uspto-grants-2016_05
Patent number
US09334464B2

Reaction notes

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