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

HRID 479324

Reaction equation

HRID 479324 reaction equation
[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

Participants

8

Reactant 5

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

Product 2

HCID 700377464,4-Di methyl-5alpha-cholesta-8,14,24-trien-3-oneYield 51.7%HCID 178460676HCID 178460676, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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%).

Workup

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

Sources & evidence

ORD record
ord-06c62459272d4f0c8c49c09c42202482
Source dataset
uspto-grants-2003_11
Patent number
US06645953B2

Linked notes

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