丙二酸二甲酯 → METHYL 2-HYDROXY-4-OXO-6-PENTYLCYCLOHEX-2-ENE-1-CARBOXYLATE

HRID 2201166笔记

反应方程式

HRID 2201166 反应方程式
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]

参与物

5

反应物 3

HCID 7943丙二酸二甲酯HCID 266303-壬烯-2-酮HCID 10942334甲醇钠

产物 1

HCID 2785071METHYL 2-HYDROXY-4-OXO-6-PENTYLCYCLOHEX-2-ENE-1-CARBOXYLATE收率 92%

试剂、催化剂与溶剂 1

HCID 887(5BETA,17BETA)-17-羟基-17-(甲基-D3)-2'H-雄甾-2-烯并[3,2-C]吡唑-5'(1'H)-酮溶剂

实验过程

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).

后处理

  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

来源与证据

ORD记录
ord-d8da0fb240ff4ba7b791d79607b5acbd
来源数据集
uspto-grants-2016_06
专利号
US09359625B2

反应笔记

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