Dodecanoyl chloride → CH3(CH2)10C(O)Och2C=C-C=cch2OC(O)(CH2)10N3

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Reaction Steps

In a glass reaction vessel, 400 milligrams (3.75 mmol) HOCH2C≡C—C≡CCH2OH prepared in Step 1, was dissolved in a mixture of 25 milliliters THF and 1 milliliters pyridine. To this stirred solution was added 1.0 gram (4.1 mmol) N3(CH2)10C(O)Cl prepared in Step 2, and 950 μL (4.1 mmol) CH3(CH2)10C(O)Cl. The resulting mixture was stirred for 3 h, concentrated, dissolved into hexanes and filtered to remove the salts. The filtrate was concentrated and purified using column chromatography eluting with 10% by volume of ethyl acetate in hexanes to yield 750 milligrams CH3(CH2)10C(O)OCH2C≡C—C≡CCH2OC(O)(CH2)10N3. In a glass reaction vessel, 280 milligrams (0.56 mmol) CH3(CH2)10C(O)OCH2C≡C—C≡CCH2OC(O)(CH2)10N3 was dissolved in 1 milliliters water and 8 milliliters THF. To this solution, 350 milligrams (1.3 mmol) triphenylphosphine was added. After 20 h of stirring, hydrogen chloride gas was bubbled through the mixture for 30 seconds. The resulting solid was filtered and washed with diethyl ether to yield 150 milligrams CH3(CH2)10C(O)OCH2C≡C—C≡CCH2OC(O)(CH2)10NH3Cl.

Provenance & Evidence