Dimethylformamide → HCID 86734711, compound

HRID 2397285Notes

Reaction equation

HRID 2397285 reaction equation
[CH3:1][O-:2].[Na+].[CH3:4][CH:5]([CH2:9][CH2:10][CH2:11][CH:12]([CH3:15])[CH2:13][CH3:14])[CH2:6][CH:7]=O.CN(C)[CH:18]=[O:19]>O>[CH3:6][C:5](/[CH:9]=[CH:7]\[CH2:6][CH:5]([CH3:4])[CH2:9][CH2:10][CH2:11][CH:12]([CH3:15])[CH2:13][CH3:14])=[CH:4][C:1]([O:19][CH3:18])=[O:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 10942334Sodium MethoxideHCID 21437500HCID 21437500, compound

Product 1

HCID 86734711HCID 86734711, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium methoxide (from 200 mg. sodium and 12 ml. methanol) is added dropwise to a stirred solution of 1.8 g. of trans diethyl 3-ethoxycarbonyl-2-methylprop-2-enyl phosphonate (II; R = ethyl, R1 = methyl and R6 = ethoxy) and 1 g. of 3,7-dimethyl-1-nonanal in 50 ml. of dimethylformamide under nitrogen. The reaction mixture is left for one hour at room temperature and then water is added followed by extraction with ether. The ethereal extracts are washed with brine, dried and evaporated to yield trans/cis methyl 3,7,11-trimethyltrideca-2,4-dienoate. The isomeric mixture can be chromatographed on silica or distilled for purification. The isomeric mixture is predominantly trans at C-2,3.

Workup

  1. extractionfollowed by extraction with ether
  2. washThe ethereal extracts are washed with brine
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-eb1c45c502e04d398768020a9e76d479
Source dataset
uspto-grants-1977_05
Patent number
US04021461

Reaction notes

Loading…