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

HRID 1076962Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1076962
[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]

Komponenten

5

Edukt 3

HCID 81961Triethyl ethane-1,1,2-tricarboxylateHCID 10942334Sodium MethoxideHCID 21328875Dimethyl trans-(3-methyl-3-hydroxy-1-octenyl)cyclopropane-1-1-dicarboxylate

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-5c0170270acb49619fa01ed57c194229
Quelldatensatz
uspto-grants-1976_05
Patentnummer
US03959263

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