Ammonium Chloride → 4,4-Di methyl-5alpha-cholesta-8,14,24-trien-3-one

HRID 479324

Reaktionsgleichung

Reaktionsgleichung von HRID 479324
[Li][CH2:2][CH2:3][CH2:4]C.[Br-].[CH:7]([P+:10]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH3:9])[CH3:8].[PH5].[O:30]=[C:31]1[CH2:53][CH2:52][C@@:51]2([CH3:54])[C@@H:33]([CH2:34][CH2:35][C:36]3[C:37]4[C@:47]([CH3:55])([CH2:48][CH2:49][C:50]=32)[C@@H:40]([C@H:41]([CH3:46])[CH2:42][CH2:43][CH:44]=O)[CH2:39][CH:38]=4)[C:32]1([CH3:57])[CH3:56].[Cl-].[NH4+]>C1COCC1>[CH:7]([PH:10]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([CH3:9])[CH3:8].[CH3:56][C:32]1([CH3:57])[C:31](=[O:30])[CH2:53][CH2:52][C@@:51]2([CH3:54])[C@H:33]1[CH2:34][CH2:35][C:36]1[C:37]3[C@:47]([CH3:55])([CH2:48][CH2:49][C:50]=12)[C@@H:40]([C@H:41]([CH3:46])[CH2:42][CH2:43][CH:44]=[C:3]([CH3:4])[CH3:2])[CH2:39][CH:38]=3

Komponenten

8

Edukt 5

HCID 25517Ammonium ChlorideHCID 2795292Isopropyltriphenylphosphonium bromideHCID 155430933-Oxo-4,4-dimethyl-5alpha-chola-8,14-dien-24-aldehydeHCID 178418339ButyllithiumHCID 178527699HCID 178527699, Verbindung

Produkt 2

HCID 700377464,4-Di methyl-5alpha-cholesta-8,14,24-trien-3-oneAusbeute 51,7 %HCID 178460676HCID 178460676, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of isopropyltriphenylphosphorane was prepared by addition of BuLi (0.16 ml of 1.6M in hexanes, 0.26 mmol) to a suspension of isopropyltriphenylphosphonium bromide (98 mg, 0.26 mmol) in THF (2 mL) at ice bath temperature. The corresponding deep red phosphorane solution was stirred a further 0.5 hour and then added dropwise via syringe to a solution of 3-oxo-4,4-dimethyl-5α-chola-8,14-dien-24-aldehyde (71 mg, 0.18 mmol) in THF (2ml) at −78° C. and stirred 2 hours before slowly warming to room temperature and stirring overnight. Saturated ammonium chloride (3 mL) was added and the aqueous phase extracted using diethyl ether, and the organic phase dried over anhydrous sodium sulphate. Flash chromatography (Eluant: 6 hexane: 1 ethyl acetate) gave the title compound (38 mg, 50%).

Aufarbeitung

  1. stirringstirring overnight
  2. extractionthe aqueous phase extracted
  3. dry with materialthe organic phase dried over anhydrous sodium sulphate

Quellen und Nachweise

ORD-Eintrag
ord-06c62459272d4f0c8c49c09c42202482
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06645953B2

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