Dimethyl malonate → Methyl 2-hydroxy-4-oxo-6-pentylcyclohex-2-ene-1-carboxylate

HRID 1055492

반응식

HRID 1055492 반응식
C[O-].[Na+].[C:4]([O:11][CH3:12])(=[O:10])[CH2:5][C:6]([O:8]C)=O.[CH3:13][C:14](=[O:22])[CH:15]=[CH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>CO>[CH2:17]([CH:16]1[CH:5]([C:4]([O:11][CH3:12])=[O:10])[C:6]([OH:8])=[CH:13][C:14](=[O:22])[CH2:15]1)[CH2:18][CH2:19][CH2:20][CH3:21]

참가 물질

5

반응물 3

HCID 7943Dimethyl malonateHCID 26630Non-3-en-2-oneHCID 10942334Sodium Methoxide

생성물 1

HCID 2785071Methyl 2-hydroxy-4-oxo-6-pentylcyclohex-2-ene-1-carboxylate수율 92%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a stirring solution of sodium methoxide (32.4 g, 0.60 mol) and dimethyl malonate (90 g, 0.68 mol) in 230 mL of anhydrous methanol was added portion wise 75 g (0.48 mol) of 90% 3-nonen-2-one. The reaction mixture was then refluxed for 3 h under N2 and allowed to cool to room temperature. The solvent was distilled under reduced pressure and the residue dissolved in 350 mL of water. The slurry of white crystals and the almost clear solution was extracted thrice with 80 mL of chloroform. The aqueous layer was acidified to pH 4 with concentrated HCl and the white precipitate that formed was allowed to stand overnight prior to filtration. The crystals were dried at 50° C. under high vacuum for 5 hours to yield 106.5 g (0.4416 mol) (92%) of methyl 6-n-Pentyl-2-hydroxy-4-oxo-cyclohex-2-ene-1-carboxylate (mp 96-98 C). The product was recrystallized using a mixture of petroleum ether:ethyl acetate (9:1), and gave 94 g of pure methyl 6-n-Pentyl-2-hydroxy-4-oxo-cyclohex-2-ene-1-carboxylate (melting point of 98-100 C).

후처리

  1. temperatureThe reaction mixture was then refluxed for 3 h under N2
  2. distillationThe solvent was distilled under reduced pressure
  3. dissolutionthe residue dissolved in 350 mL of water
  4. extractionThe slurry of white crystals and the almost clear solution was extracted thrice with 80 mL of chloroform
  5. customthe white precipitate that formed
  6. filtrationto filtration
  7. customThe crystals were dried at 50° C. under high vacuum for 5 hours

출처 및 근거

ORD 기록
ord-e1606eb73a2545e49f73a42a1363d667
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394510B2

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