Sodium hydride → HCID 23046167, compound

HRID 2107645Notes

Reaction equation

HRID 2107645 reaction equation
[H-].[Na+].[CH3:3][CH2:4][O:5][C:6](/[CH:8]=[CH:9]/[CH2:10]P(OCC)(OCC)=O)=[O:7].[CH3:19][O:20][CH2:21][CH2:22][O:23][CH2:24][O:25][C:26]1[C:33]([CH3:34])=[CH:32][C:29]([CH:30]=O)=[CH:28][C:27]=1[CH3:35]>O1CCCC1>[CH3:19][O:20][CH2:21][CH2:22][O:23][CH2:24][O:25][C:26]1[C:33]([CH3:34])=[CH:32][C:29](/[CH:30]=[CH:10]/[CH:9]=[CH:8]/[C:6]([O:5][CH2:4][CH3:3])=[O:7])=[CH:28][C:27]=1[CH3:35]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 5365783Triethyl 4-phosphonocrotonate, mixture of isomersHCID 23046188HCID 23046188, compound

Product 1

HCID 23046167HCID 23046167, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of 60% sodium hydride (1.01 g) in dry tetrahydrofuran (60 ml), 80% triethyl 4-phosphonocrotonate (6.57 g) was added dropwise below 10° C. under an inert atmosphere. After being stirred for 30 minutes, a solution of 4-[(2-methoxyethoxy)methoxy]-3,5-dimethylbenzaldehyde (5.0 g) in dry tetrahydrofuran (50 ml) was added thereto below 10° C. After stirring for 2 hours, the reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (100 ml), washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The solvent was distilled off and the residue was subjected to column chromatography on silica gel (130 g) and eluted with a mixture of n-hexane and ethyl acetate (7:3 V/V). The fractions containing the object compound were combined and concentrated under reduced pressure to give a syrup of ethyl 5-[4-{(2-methoxyethoxy)methoxy}-3,5-dimethylphenyl]-(2E,4E)-2,4-pentadienoate (5.28 g).

Workup

  1. additionwas added dropwise below 10° C. under an inert atmosphere
  2. custombelow 10° C
  3. stirringAfter stirring for 2 hours
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in ethyl acetate (100 ml)
  6. washwashed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. distillationThe solvent was distilled off
  9. washeluted with a mixture of n-hexane and ethyl acetate (7:3 V/V)
  10. additionThe fractions containing the object compound
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-252872468b904f0d8063a977c66c2606
Source dataset
uspto-grants-1990_06
Patent number
US04935432

Reaction notes

Loading…