Water → (E)-3-(5-ethyl-4-hydroxy-3-methoxy-1-naphthyl)-2-methylpropenoic acid

HRID 488127Notes

Reaction equation

HRID 488127 reaction equation
[H-].[Na+].CC[O:5][C:6]([CH:8](P(OCC)(OCC)=O)[CH3:9])=[O:7].[CH2:18]([C:20]1[CH:29]=[CH:28][CH:27]=[C:26]2[C:21]=1[C:22]([O:34]COC)=[C:23]([O:32][CH3:33])[CH:24]=[C:25]2[CH:30]=O)[CH3:19].O>CN(C)C=O>[CH2:18]([C:20]1[CH:29]=[CH:28][CH:27]=[C:26]2[C:21]=1[C:22]([OH:34])=[C:23]([O:32][CH3:33])[CH:24]=[C:25]2/[CH:30]=[C:8](\[CH3:9])/[C:6]([OH:5])=[O:7])[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 107155Triethyl 2-phosphonopropionateHCID 99705695-Ethyl-3-methoxy-4-methoxymethoxy-1-naphthalenecarbaldehyde

Product 1

HCID 6509859(E)-3-(5-ethyl-4-hydroxy-3-methoxy-1-naphthyl)-2-methylpropenoic acidYield 122%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

36 g of 60% sodium hydride was suspended in 500 ml of N,N-dimethylformamide and 268 g of triethyl 2-phosphonopropionate was added at ice bath temperature. After stirring at room temperature for 1 hour, a solution of 206 g of 5-ethyl-3-methoxy-4-methoxymethoxy-1-naphthalenecarbaldehyde was added. After stirring at room temperature for 15 minutes, ice cooled water was gradually added at ice bath temperature. The mixture was extracted with ethyl acetate and the combined organic layer was washed with brine. After drying over anhydrous magnesium sulfate, the solvent was evaporated and the residue was purified by silica gel column chromatography (10% ethyl acetate/hexane) to obtain 262.4 g of the titled compound as a yellow oil (containing a small amount of Z isomer).

Workup

  1. stirringAfter stirring at room temperature for 15 minutes
  2. additionwas gradually added at ice bath temperature
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe combined organic layer was washed with brine
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. customthe solvent was evaporated
  7. customthe residue was purified by silica gel column chromatography (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4f1aa77bad7c4150b8651deb1344b99e
Source dataset
uspto-grants-1994_03
Patent number
US05298649

Reaction notes

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