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

HRID 614304

Reaction equation

HRID 614304 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0c1645e9c1e34a4e9898d495d1cff07b
Source dataset
uspto-grants-1979_03
Patent number
US04144251

Linked notes

Loading…