Methane → HCID 86734121, compound

Participants

Reaction Steps

In the above reaction scheme, the starting material IV is readily prepared from the corresponding bromo- or iodo-derivatives which are commercially available; in IV, R1 can be hydrogen, loweralkyl of 1 to 3 carbon atoms, loweralkoxy of 1 to 3 carbon atoms, fluoro, chloro, trifluoromethyl, phenyl or phenoxy. Intermediate V is prepared by reacting cuprious-n-propyl acetylide (prepared according to Castro et al., J. Org. Chem., 31: 4071 [1966]) and hexamethylphosphorus triamide copper iodide, VI. Compound VI is prepared as follows: (1) add 18.39 g of purified CuI (Inorg. Synth., 7: 9 [ 1963]) to 177 g KI in 135 ml. H2O and stir with activated charcoal (Norite); (2) filter the solution through infusorial earth (Celite) and add 14.5 g (0.089 mole) of hexamethylphosphorous triamide (commercially available) under argon atmosphere; (3) filter, wash with aqueous KI and H2O; (4) dissolve product in dry ether, filter, remove ether in vacuo to obtain 13.85 g hexamethylphosphorous triamide copper (I) iodide:NMR (COCl3): singlet, δ 2.65. Compound VII, 15α-ethoxyethoxy-PGA-methyl ester is prepared from 15-α-hydroxy-PGA, which is available from coral extracts or which can be synthesized according to the Corey or Sih procedures (Corey et al., J. Am. Chem. Soc., 91: 5675 [1969]; Sih et al., J. Am. Chem. Soc., 95: 1676 [1973]).

Provenance & Evidence