Organic Lab Reactions 220

Organic Lab Reactions 220 - nol-1...

Info iconThis preview shows page 1. Sign up to view the full content.

View Full Document Right Arrow Icon
REDUCTION OF KETONES 215 TABLE II— Continued REDUCTION OF RETONES WITH ALUMINUM ISOPROPOXIDE Compound Reduced Ergostatrien-4,7,22- one-3 Ergostatetraen-4,7,9- (ll),22-one-3 Lumistatrienone-3 Zymostenone 4-Dehydrotigogenone-3 Lanostenone Product Formed Ergostatrien-4,7,22-ol-3 (45%) epi-Ergostatrien-4,7,22- ol-3 (35%) Ergostatrien-5,7,22-ol-3 (19%) epi-Ergostatrien-5,7,22- ol-3 (1%) (estimated ratios) Mixture of ergostate- traenols-3 Mixture of lumistatri- enols Zymostenol epi-4-Dehydrotigogenol-3 Lanosterol Reagent and Solvent * D D D D D Yield 100% 73% 22% Refer- ence 32,33, 129, 130 32 32 131 .132 133 (e) a-Halogen Substituted Ketones 1,1,1-Trichloroacetone a-Bromoacetophenone a,a,a-Trichloroaceto- phenone a-Bromopropiophenone a-Bromoisobutyrophe- none 2-Bromocyclohexanone 2-Bromocholesten-4- "one-3 1,1,1 -Trichloropropanol-2 ( 2-Bromo-l-phenyletha-
Background image of page 1
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: nol-1 2,2,2-Trichloro-l-phenyl-ethanoH 2-Bfomo-l-phenyl-pro-panol-1 (and other prod-ucts—see p. 193) • Little bromohydrin (see p. 193 for products) l-Phenyl-2-methyl-3-bromopropene-1 (see p. 194) 2-Bromocyolohexanol (cyclohexanol 33%) Little bromine in product A1(OC S H 8 )3 C A1(OC 2 H 6 )3 U U (100°) U (33°) U u 67% 85% 69% 35-42% — 42% 30% — ' 2 5 2 43, 44 44,45 44 46 44 ' Nora: References 81-158 appear on pp. 221-223. * Unless otherwise stated, the reduction was carried out with aluminum isopropoxide in boiling iso-propyl alcohol solution. C refers to clarified but undistilled aluminum isopropoxide; D, to distilled reagent; and U, to an untreated solution of the alkoxide (see p. 199)....
View Full Document

This note was uploaded on 11/20/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

Ask a homework question - tutors are online