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Acetic Acid → 6-[(E)-3-tert-butyldimethylsilyloxy-4-phenoxybut-1-enyl]-3-(1-hydroxy-4-methoxycarbonylbut-1-yl)bicyclo[3,3,0]octan-2-one

HRID 462801
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 462801
[Si:1]([O:8][CH:9]([CH2:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)/[CH:10]=[CH:11]/[CH:12]1[CH2:19][CH2:18][CH:17]2[CH:13]1[CH2:14][CH2:15][C:16]2=[O:20])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:39][O:40][C:41]([CH2:43][CH2:44][CH2:45][CH:46]=[O:47])=[O:42].C(O)(=O)C>O1CCCC1.C(OCC)C.O>[Si:1]([O:8][CH:9]([CH2:21][O:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)/[CH:10]=[CH:11]/[CH:12]1[CH2:19][CH2:18][CH:17]2[CH:13]1[CH2:14][CH:15]([CH:46]([OH:47])[CH2:45][CH2:44][CH2:43][C:41]([O:40][CH3:39])=[O:42])[C:16]2=[O:20])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 176Acetic AcidHCID 554053Pentanoic acid, 5-oxo-, methyl esterHCID 2733832Lithium hexamethyldisilazaneHCID 20397195(E)-2-(3-tert-butyldimethylsilyloxy-4-phenoxybut-1-enyl)bicyclo[3,3,0]octan-6-one

Produkt 1

HCID 203972146-[(E)-3-tert-butyldimethylsilyloxy-4-phenoxybut-1-enyl]-3-(1-hydroxy-4-methoxycarbonylbut-1-yl)bicyclo[3,3,0]octan-2-one
Ausbeute 47,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

A stirred solution of (E)-2-(3-tert-butyldimethylsilyloxy-4-phenoxybut-1-enyl)bicyclo[3,3,0]octan-6-one (75 mg), prepared as described in Reference Example 46 and in the form of (±)-(E)-2β-(3β-tert-butyldimethylsilyloxy-4-phenoxybut-1-enyl)bicyclo[3,3,0]octan-6-one, in dry tetrahydrofuran (2.55 ml) was cooled to -70° C. under an atmosphere of argon and treated with a solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (1M; 0.204 ml), and the mixture was stirred at -70° C. for 10 minutes. The mixture was then treated with 4-methoxycarbonylbutanal (44 mg) and stirred for a further period of 150 minutes at -70° C. The mixture was then treated with a solution of glacial acetic acid (0.019 ml) in diethyl ether (0.17 ml) and allowed to warm to the ambient temperature. The mixture was treated with water (25 ml) and extracted with ethyl acetate. The extract was washed with saturated aqueous sodium bicarbonate solution, and with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulphate, and concentrated under reduced pressure. The residual oil was subjected to medium pressure, short column chromatography on silica gel, eluting with a mixture of ethyl acetate and hexane (1:2 v/v), to give 6-[(E)-3-tert-butyldimethylsilyloxy-4-phenoxybut-1-enyl]-3-(1-hydroxy-4-methoxycarbonylbut-1-yl)bicyclo[3,3,0]octan-2-one (47 mg), in the form of (±)-6β-[(E)-3β-tert-butyldimethylsilyloxy-4-phenoxybut-1-enyl]-3-(1-hydroxy-4-methoxycarbonylbut-1-yl)bicyclo[3,3,0]octan-2-one.

Aufarbeitung

  1. stirringstirred for a further period of 150 minutes at -70° C
  2. temperatureto warm to the ambient temperature
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated aqueous sodium bicarbonate solution
  5. dry with materialwith saturated aqueous sodium chloride solution, dried over anhydrous sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. washeluting with a mixture of ethyl acetate and hexane (1:2 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-0459a8ac3b12418c87674bc3732b0590
Quelldatensatz
uspto-grants-1985_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04517202

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