Diisobutylaluminumhydride → (2z)-2-((3r,5s)-3-{[Tert-butyl(diphenyl)silyl]oxy}-5-fluoro-4-methylenecyclohexylidene)ethanol

HRID 388740

Reaktionsgleichung

Reaktionsgleichung von HRID 388740
[Si:1]([O:18][C@H:19]1[C:24](=[CH2:25])[C@@H:23]([F:26])[CH2:22]/[C:21](=[CH:27]\[C:28](OCC)=[O:29])/[CH2:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C>ClCCl.C1(C)C=CC=CC=1>[Si:1]([O:18][C@H:19]1[C:24](=[CH2:25])[C@@H:23]([F:26])[CH2:22]/[C:21](=[CH:27]\[CH2:28][OH:29])/[CH2:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 21225700DiisobutylaluminumhydrideHCID 57696867Ethyl (2z)-((3r,5s)-3-{[tert-butyl(diphenyl)silyl]oxy}-5-fluoro-4-methylenecyclohexylidene)acetate

Produkt 1

HCID 68936398(2z)-2-((3r,5s)-3-{[Tert-butyl(diphenyl)silyl]oxy}-5-fluoro-4-methylenecyclohexylidene)ethanolAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21877217Toluene methylene chlorideLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

The compound of Example 13G (40 mg, 0.09 mmol) was dissolved in 1 mL of 1:1 dichloromethane/toluene and cooled to −78° C. Diisobutylaluminum hydride (1 M in hexanes, 0.36 mL) was added, and the mixture was stirred for 20 minutes. The reaction was quenched by the addition of water; the mixture was warmed to ambient temperature, and then acidified to pH˜2 by addition of concentrated HCl. The mixture was extracted with ethyl acetate; the organics were washed with brine and dried over Na2SO4. The solvents were removed in vacuo; the residue was purified by chromatography on an Analogix Intelliflash 280™, eluting with 17% ethyl acetate in hexanes to give the titled compound (25 mg, 68%).

Aufarbeitung

  1. customThe reaction was quenched by the addition of water
  2. temperaturethe mixture was warmed to ambient temperature
  3. additionacidified to pH˜2 by addition of concentrated HCl
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe organics were washed with brine
  6. dry with materialdried over Na2SO4
  7. customThe solvents were removed in vacuo
  8. customthe residue was purified by chromatography on an Analogix Intelliflash 280™
  9. washeluting with 17% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-7e5502f2a60548b8a139903ef04181b0
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08377913B2

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