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

HRID 479324

反応式

HRID 479324 の反応式
[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

参加物

8

反応物 5

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

生成物 2

HCID 700377464,4-Di methyl-5alpha-cholesta-8,14,24-trien-3-one収率 51.7%HCID 178460676HCID 178460676、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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%).

後処理

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

出典と根拠

ORDレコード
ord-06c62459272d4f0c8c49c09c42202482
出典データセット
uspto-grants-2003_11
特許番号
US06645953B2

関連ノート

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