Triethyl ethane-1,1,2-tricarboxylate → Dimethyl trans-1-(Carboethoxymethyl)-5-(3-hydroxy-3-methyl-1-octenyl)-2-oxo-1,3-cyclopentanedicarboxylate

HRID 614304

반응식

HRID 614304 반응식
[CH:1]([C:13]([O:15]CC)=O)([C:8]([O:10][CH2:11]C)=[O:9])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].C[O-].[Na+].[CH3:21][C:22]([OH:41])([CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])/[CH:23]=[CH:24]/[CH:25]1[CH2:27][C:26]1(C(OC)=O)[C:28]([O:30][CH3:31])=[O:29]>CO>[C:3]([CH2:2][C:1]1([C:8]([O:10][CH3:11])=[O:9])[C@@H:25]([CH:24]=[CH:23][C:22]([OH:41])([CH3:21])[CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH2:27][C@H:26]([C:28]([O:30][CH3:31])=[O:29])[C:13]1=[O:15])([O:5][CH2:6][CH3:7])=[O:4]

참가 물질

5

반응물 3

HCID 81961Triethyl ethane-1,1,2-tricarboxylateHCID 10942334Sodium MethoxideHCID 21328875HCID 21328875, 화합물

생성물 1

HCID 70601158Dimethyl trans-1-(Carboethoxymethyl)-5-(3-hydroxy-3-methyl-1-octenyl)-2-oxo-1,3-cyclopentanedicarboxylate

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of triethyl 1,1,2-ethanetricarboxylate (1.36 g) in 3 ml of methanol, a freshly prepared solution of sodium methoxide (from 0.126 g of sodium and 6 ml of absolute methanol) is added. The mixture is heated to 80°. A solution of dimethyl trans-(3-methyl-3-hydroxy-1-octenyl)cyclopropane-1-1-dicarboxylate (1.7 g) is gradually added and the resulting mixture stirred for an additional 15 min. The methanol is removed by distillation at reduced pressure. The residue is then heated at 100° for 45 min. Thereafter the mixture is cooled in an ice bath and rendered neutral with acetic acid. The mixture is extracted with ether. The extract is dried (Na2SO4) and concentrated. Chromatography of the residue on silica gel using ethyl acetate/benzene (1:4) as eluant gives the title compound, νmaxfilm 3350, 1727 cm-1.

후처리

  1. temperatureThe mixture is heated to 80°
  2. customThe methanol is removed by distillation at reduced pressure
  3. temperatureThe residue is then heated at 100° for 45 min
  4. temperatureThereafter the mixture is cooled in an ice bath
  5. extractionThe mixture is extracted with ether
  6. dry with materialThe extract is dried (Na2SO4)
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-0c1645e9c1e34a4e9898d495d1cff07b
출처 데이터셋
uspto-grants-1979_03
특허 번호
US04144251

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