Water → ethyl (E)-3-(5-ethyl-3-methoxy-4-methoxymethoxy-1-naphthyl)-2-methylpropenoate

HRID 654704Notes

Reaction equation

HRID 654704 reaction equation
[H-].[Na+].[CH3:3][CH2:4][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][CH2:35][O:36][CH3:37])=[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]([O:34][CH2:35][O:36][CH3:37])=[C:23]([O:32][CH3:33])[CH:24]=[C:25]2/[CH:30]=[C:8](\[CH3:9])/[C:6]([O:5][CH2:4][CH3:3])=[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 9975669ethyl (E)-3-(5-ethyl-3-methoxy-4-methoxymethoxy-1-naphthyl)-2-methylpropenoateYield 97.5%

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-ec01aa74e4ed41ca9dc3719d913c064f
Source dataset
uspto-grants-1992_07
Patent number
US05134111

Reaction notes

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