Water → HCID 54235447, compound

HRID 703902Notes

Reaction equation

HRID 703902 reaction equation
[CH3:1][C:2](C)([O-])C.[K+].COC[O:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][C:12]=1[CH:21]=O.O.[C:24]([O:27][CH2:28][CH3:29])(=[O:26])[CH3:25]>O1CCCC1>[OH:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][C:12]=1[CH:21]=[CH:1][CH2:2][CH2:25][C:24]([O:27][CH2:28][CH3:29])=[O:26]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 125362801-(Methoxymethoxy)-2-naphthalenecarboxaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 54235447HCID 54235447, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of potassium t-butoxide (2.10 g, 0.019 mole) and 4-carbethoxypropyl-triphenylphosphonium bromide (prepared according to the procedure of P. E. Sonnet, J. Org. Chem. 34, 1147 (1964); 8.40 g, 0.018 mole) in dry tetrahydrofuran (15 mL) was stirred at 0°. After 45 minutes, a solution of 1-methoxymethoxy-2-naphthaldehyde (2.00 g, 0.009 mole) in dry tetrahydrofuran (7.5 mL) was added over 10 minutes. The resulting mixture was stirred at 0° for 2 hours, then was poured into water. The crude material was isolated by extraction with ethyl acetate and chromatographed with 10% ether/petroleum ether, then was dissolved in absolute ethanol (200 mL), treated with 3 drops of sulfuric acid, and heated at reflux for 18 hours. After cooling, the solution was diluted with water and the crude product mixture isolated by extraction with ethyl acetate. This was chromatographed with 85:15 petroleum ether/ether to provide two different solids. The first one to elute was recrystallized (hexane) to provide the Z isomer of the title compound (0.43 g, 17%) as a pale yellow solid, mp 75°-77°. The second solid was recrystallized (hexane) to provide the E isomer (0.23 g, 9%) as a white solid, mp 63°-64°.

Workup

  1. customprepared
  2. customchromatographed with 10% ether/petroleum ether
  3. dissolutionwas dissolved in absolute ethanol (200 mL)
  4. additiontreated with 3 drops of sulfuric acid
  5. temperatureheated
  6. temperatureat reflux for 18 hours
  7. temperatureAfter cooling
  8. additionthe solution was diluted with water
  9. customthe crude product mixture isolated by extraction with ethyl acetate
  10. customThis was chromatographed with 85:15 petroleum ether/ether
  11. customto provide two different solids
  12. washThe first one to elute
  13. customwas recrystallized (hexane)

Sources & evidence

ORD record
ord-daaf14b38d08449e8a52148667bc7f2a
Source dataset
uspto-grants-1991_01
Patent number
US04985435

Reaction notes

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