Hydrochloric Acid → HCID 54022973, compound

HRID 703901Notes

Reaction equation

HRID 703901 reaction equation
[H-].[Na+].COC[O:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1[CH:17]=O.[Br-].[C:20]([CH2:23][CH2:24][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:22])=[O:21].Cl.O1CC[CH2:47][CH2:46]1>CS(C)=O.C(O)C.S(=O)(=O)(O)O.O.C(OCC)(=O)C>[OH:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1[CH:17]=[CH:24][CH2:23][C:20]([O:22][CH2:46][CH3:47])=[O:21]

Participants

11

Reactant 5

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 2733850(2-Carboxyethyl)triphenylphosphonium bromideHCID 125362801-(Methoxymethoxy)-2-naphthalenecarboxaldehyde

Product 1

HCID 54022973HCID 54022973, compoundYield 15%

Reagents, catalysts & solvents 5

HCID 1118Sulfuric AcidCatalystHCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A suspension of sodium hydride (60% in mineral oil; 1.94 g, 0.049 mole) in dry tetrahydrofuran (20 mL) was stirred at 0°. A solution of 1-methoxymethoxy-2-naphthaldehyde (2.00 g, 0.009 mole) and 2-carboxyethyl-triphenylphosphonium bromide(prepared by the procedure of H. S. Corey, J. R. D. McCormick, and W. E. Swensen, J. Am. Chem. Soc. 86, 1884 (1964); 9.60 g, 0.023 mole) in dry dimethyl sulfoxide (15 mL) was added over 20 minutes. The mixture was allowed to warm to room temperature over 1.25 hours, then stirred at room temperature for 30 minutes. 1.0N hydrochloric acid (10 mL) was added dropwise, followed by stirring for an additional 20 minutes. The crude material was isolated by extraction with ethyl acetate and dissolved in absolute ethanol (200 mL), treated with 10 drops of concentrated sulfuric acid, and heated at reflux for 6 hours. The cooled solution was diluted with water, and the crude product isolated by extraction with ethyl acetate. The resulting oil was chromatographed with 9:1 petroleum ether/ether, to provide a solid which was recrystallized (hexane) to give the title compound (0.35 g, 15%) as a tan solid, mp 83°-84°.

Workup

  1. stirringstirred at room temperature for 30 minutes
  2. stirringby stirring for an additional 20 minutes
  3. temperatureheated
  4. temperatureat reflux for 6 hours
  5. customThe resulting oil was chromatographed with 9:1 petroleum ether/ether
  6. customto provide a solid which
  7. customwas recrystallized (hexane)

Sources & evidence

ORD record
ord-4feed4852e8d41dca3b7392d557fb384
Source dataset
uspto-grants-1991_01
Patent number
US04985435

Reaction notes

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