Ammonium Chloride → HCID 54559612, compound

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Reaction Steps

A 50 ml oven-dried 2-necked (14/20) round bottom flask, equipped with magnetic stirring bar, nitrogen inlet and serum cap is charged with methoxymethyltriphenylphosphonium chloride (90%) (2.5 g). This material is suspended in 10 ml tetrahydrofuran and the resulting mixture is placed under a nitrogen atmosphere and cooled to 0°-5° C. n-Butyllithium reagent (1.65M in hexane, 4.0 ml) is added dropwise to the stirred mixture via syringe over 2-3 min. The solids gradually dissolve to give a deep red colored solution (some solids remain). This solution is stirred at 0°-5° C. for 30 min and then is treated with a solution of 2-(2-formylethyl)-4-methoxy-1-[(tetrahydro-2H-pyran-2-yl)oxy]naphthalene (0.958 g) in 5 ml tetrahydrofuran in one portion. The resulting deep red colored solution is stirred at 0°-5° C. for 15 min at which time TLC analysis indicates no remaining starting material. The solution is poured into saturated aqueous ammonium chloride, the pH adjusted to 7 with 10% sodium bisulfate and this mixture extracted first with Skellysolve B and then with ether. Each of these extracts is washed two times with water, dried with magnesium sulfate, filtered and concentrated. TLC analysis of the ether extract indicates the presence of the product mixture suggesting that the Skellysolve B extraction is not efficient. The separate extracts are combined to give 1.36 g of the title compound mixture.

Provenance & Evidence