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Organic Lab Reactions 225

Organic Lab Reactions 225 - carboxylic acid(a-Methyl...

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220 REDUCTION WITH ALUMINUM ALKOXIDES TABLE II— Continued REDUCTION or KETONES WITH ALUMINUM ISOPBOPOXIDE Compound Reduced Methyl ,8-(2-naphthoyl-) propionate Methyl fluorenone-2-car- boxylate Isopropyl fluorenone-3- carboxylate Isopropyl anthraqui- none-2-carboxylate Methyl l-keto-1,2,3,4- tetrahydrophenan- threne-2-acetate Methyl l-keto-2-methyl- 1,2,3,4-tetrahydrophe- nanthrene-2-car- boxylate Methyl 3-ketocholen-ll- ate Methyl ester of A 5 -7- ketocholenic acid Zinc complex of methyl- pheophorbide a Methylpyropheo- phorbide a Dimethyl ester of pheo- porphyrin OB Trimethyl ester of 2,a- ketochloroporphyrin Trimethyl ester of 2- desvinyl-2-acetyl- chlorin ee Product Formed 7-(2-Naphthyl-)Y-bu- tyrolactone Isopropyl fluorenol-2- carboxylate Isopropyl fluorenol-3- carboxylat.e Isopropyl anthrahydro- quinone-2-carboxylate Lactone of 1-hydroxy-l,- 2,3,4-tetrahydrophe- nanthrene-2-acetic acid Isopropyl esters of stereo- isomeric l-hydroxy-2- methyl-1,2,3,4-tetra- hydrophenanthrene-2-
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Unformatted text preview: carboxylic acid (a-Methyl 3-hydroxycholen-11-ate (after remethyla-tion), a isomer = 46%, 0 isomer = 32% A 6 ' 7-Choladienic acid (after hydrolysis) 9-Hydroxydesoxometh-ylpheophorbide a 9-Hydroxydesoxometh-ylpyropheophorbide a Dimethyl ester of 9-hy-droxydesoxopheopor-phyrin as Trimethyl ester of 2,a-hydroxy chloropor-phyrin 66 Trimethyl ester of 2,a-hydroxymesochlorin ee Reagent and Solvent * U D D D ' D U D D C C C C N c Yield 97% 85%-71% 55% 80% 91% 78% 90% 5% 50% — "Good" • — Refer-ence 41 36 36 74 37 41 157 158 2*2 22 22 22 22 NOTB: References 81-168 appear on pp. 221-223. * Unless otherwise stated, the reduction was carried out with aluminum isopf opoxide in boiling ifio-propyl alcohol solution. C refers to clarified but uadintilled aluminum isopropoxide; D, to distilled reagent; and IT, to an untreated solution of the nlkocde (gee p. 199)....
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