Dimethylformamide → Ethyl 11-mercapto-3,7,11-trimethyldodeca-2,4-dienoate

HRID 1605139Notes

Reaction equation

HRID 1605139 reaction equation
[SH:1][C:2]([CH3:12])([CH3:11])[CH2:3][CH2:4][CH2:5][CH:6]([CH3:10])[CH2:7][CH:8]=O.[CH2:13]([O:15][C:16]([CH:18]=[C:19]([CH3:31])[CH2:20]P(=O)(OC(C)C)OC(C)C)=[O:17])[CH3:14].CN(C)C=O.[OH-].[Na+]>CCCCCC.O>[SH:1][C:2]([CH3:11])([CH3:12])[CH2:3][CH2:4][CH2:5][CH:6]([CH3:10])[CH2:7][CH:8]=[CH:20][C:19]([CH3:31])=[CH:18][C:16]([O:15][CH2:13][CH3:14])=[O:17]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 215493457-Mercapto-3,7-dimethyloctan-1-alHCID 54005430Ethyl 4-(diisopropoxy-phosphoryl)-3-methylbut-2-enoate

Product 1

HCID 54474469Ethyl 11-mercapto-3,7,11-trimethyldodeca-2,4-dienoate

Reagents, catalysts & solvents 1

HCID 22114717Water hexaneSolvent

Procedure

A mixture of 5 g. of 7-mercapto-3,7-dimethyloctan-1-al 8.5 g. of di-isopropyl 3-ethoxycarbonyl-2-methylprop-2-enyl-phosphonate, and 40 ml. of dimethylformamide, under nitrogen and cooled in an ice-bath, is stirred for 0.5 hours and then ground NaOH (1.165g.) is added. The reaction mixture is stirred at room temperature for 3 hours and then hexane-water (1/1) added. The organic layer is washed with water and brine, dried over calcium sulfate and concentrated. The concentrate is filitered through Florisil using hexane and hexane/ether. The filtrate is concentrated and then distilled to yield ethyl 11-mercapto-3,7,11-trimethyldodeca-2,4 -dienoate (mostly trans-2, trans-4).

Workup

  1. additionA mixture of 5 g
  2. additionis added
  3. stirringThe reaction mixture is stirred at room temperature for 3 hours
  4. washThe organic layer is washed with water and brine
  5. dry with materialdried over calcium sulfate
  6. concentrationconcentrated
  7. concentrationThe filtrate is concentrated
  8. distillationdistilled

Sources & evidence

ORD record
ord-139c9eed1963451d8d8a53c2cb1214f9
Source dataset
uspto-grants-1976_04
Patent number
US03948996

Reaction notes

Loading…