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

HRID 479324

반응식

HRID 479324 반응식
[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

참가 물질

8

반응물 5

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

생성물 2

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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%).

후처리

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

출처 및 근거

ORD 기록
ord-06c62459272d4f0c8c49c09c42202482
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06645953B2

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