Tetrahydrofuran → HCID 53903233, compound

HRID 438021Notes

Reaction equation

HRID 438021 reaction equation
[CH2:1]([O:3][C:4](=[O:9])[CH2:5][C:6]([OH:8])=O)[CH3:2].C[O-].[Mg+2].C[O-].O1CCCC1.[CH2:20]([O:38][C:39]1[S:43][C:42](C(N2C=CN=C2)=O)=[CH:41][CH:40]=1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:28]=[CH:29][CH2:30][CH:31]=[CH:32][CH2:33][CH:34]=[CH:35][CH2:36][CH3:37]>CO>[CH2:1]([O:3][C:4](=[O:9])[CH2:5][C:6]([C:42]1[S:43][C:39]([O:38][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:28]=[CH:29][CH2:30][CH:31]=[CH:32][CH2:33][CH:34]=[CH:35][CH2:36][CH3:37])=[CH:40][CH:41]=1)=[O:8])[CH3:2]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 70615Monoethyl malonateHCID 164537Methanol, magnesium salt (2:1)HCID 54539075HCID 54539075, compound

Product 1

HCID 53903233HCID 53903233, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 14.5 g (0.110 mole) of malonic acid mono ethyl ester, 19.0 g (0.220 mole) of magnesium methoxide and anhydrous tetrahydrofuran is heated with stirring under nitrogen allowing the methanol produced to distill off. To this mixture is added 45.0 g (0.105 mole) of N-[5-(9,12,15-octadecatrien-1-yloxy)-2-thenoyl]imidazole with stirring and cooling on an ice bath for four hours. The solvent is removed and the residue diluted with ice-concentrated HCl (1:1) solution to give 5-(9,12,15-octadecatrien-1-yloxy)then-2-oylacetic acid ethyl ester.

Workup

  1. temperatureis heated
  2. customproduced
  3. distillationto distill off
  4. temperaturecooling on an ice bath for four hours
  5. customThe solvent is removed
  6. additionthe residue diluted with ice-concentrated HCl (1:1) solution

Sources & evidence

ORD record
ord-508c15db3d1f461cb70b93043cdbcfd0
Source dataset
uspto-grants-1977_06
Patent number
US04032647

Reaction notes

Loading…