(5BETA,17BETA)-17-羟基-17-(甲基-D3)-2'H-雄甾-2-烯并[3,2-C]吡唑-5'(1'H)-酮 → 苯甲酰氧基乙醛缩二乙醇

HRID 31710

反应方程式

HRID 31710 反应方程式
N1C=CC=CC=1.[CH2:7]([O:9][CH:10]([O:13][CH2:14][CH3:15])[CH2:11][OH:12])[CH3:8].[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CO>C(OCC)(=O)C.O>[C:16]([O:12][CH2:11][CH:10]([O:13][CH2:14][CH3:15])[O:9][CH2:7][CH3:8])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

参与物

7

反应物 4

HCID 887(5BETA,17BETA)-17-羟基-17-(甲基-D3)-2'H-雄甾-2-烯并[3,2-C]吡唑-5'(1'H)-酮HCID 1049吡啶HCID 7412苯甲酰氯HCID 121292,2-二乙氧基乙醇

产物 1

HCID 11817258苯甲酰氧基乙醛缩二乙醇收率 96.4%

试剂、催化剂与溶剂 2

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 8857乙酸乙酯溶剂

实验过程

To a pyridine (30 ml) solution of glycol aldehyde diethylacetal (19.8 g, 148 mmol), benzoyl chloride (51.7 ml, 444 mmol) was added dropwise at −20 to 30° C. The mixture was stirred at room temperature for 167 hours and 50 minutes. After methanol and water were added to the mixture, extraction with ethyl acetate was performed. The obtained organic layer was washed with a saturated aqueous ammonium chloride solution, saturated aqueous sodium hydrogencarbonate solution, and a saturated saline solution. After dried over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and purified by silica gel column chromatography (elution solvent: heptane, ethyl acetate/heptane=1/9). Thereafter, purification by silica gel column chromatography (elution solvent: heptane, ethyl acetate/heptane=1/100, 1/30, 1/10) was performed again to obtain the title compound (34 g, yield: 96.4%) as a light green oil.

后处理

  1. washThe obtained organic layer was washed with a saturated aqueous ammonium chloride solution, saturated aqueous sodium hydrogencarbonate solution
  2. dry with materialAfter dried over anhydrous magnesium sulfate
  3. concentrationthe mixture was concentrated under reduced pressure
  4. custompurified by silica gel column chromatography (elution solvent: heptane, ethyl acetate/heptane=1/9)
  5. customThereafter, purification
  6. washby silica gel column chromatography (elution solvent: heptane, ethyl acetate/heptane=1/100, 1/30, 1/10)

来源与证据

ORD记录
ord-b344b96185124106ab3614c124b56f56
来源数据集
uspto-grants-2008_09
专利号
US07425634B2

关联笔记

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