叔丁醇 → HCID 178445820，化合物

HRID 20390

反应方程式

HRID 20390 反应方程式
[H-].[Al+3].[Li+].[H-].[H-].[H-].C(O)(C)(C)C.[H-].[C:13]([CH:17]1[CH2:20][C:19](=[O:21])[CH2:18]1)([CH3:16])([CH3:15])[CH3:14]>O1CCCC1>[C:13]([C@@H:17]1[CH2:20][C@H:19]([OH:21])[CH2:18]1)([CH3:16])([CH3:15])[CH3:14]

参与物

6

反应物 4

HCID 6386叔丁醇HCID 166653HydrideHCID 109314423-叔丁基环丁酮HCID 21226445Aluminium lithium hydride

产物 1

HCID 178445820HCID 178445820，化合物

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂

实验过程

Cool lithium aluminum hydride (16 mL, 16 mmol, 1.0 M solution in tetrahydrofuran) under a nitrogen atmosphere to 0° C. Add tert-butanol (4.6 mL, 48.1 mmol) dropwise, warm to room temperature, and stir the resulting solution for 1 hour. Cool the hydride solution to −78° C. and add a solution of 3-tert-butylcyclobutanone (1 g, 7.9 mmol) in dry tetrahydrofuran (3 mL) dropwise. Stir for 1 hour at −78° C. and then warm to room temperature over 1 hour. Slowly quench the mixture with 0.1 N hydrochloric acid. Dilute the resulting mixture with ethyl acetate and a saturated aqueous solution of sodium potassium tartrate (Rochelle salt) and stir the biphasic mixture overnight. Filter the mixture to remove precipitates and separate the aqueous layer. Saturate the aqueous phase with sodium chloride and extract with ethyl acetate. Add the organic extract to the ethyl acetate solution of the reaction mixture and wash the resultant mixture with saturated aqueous sodium chloride solution, dry (magnesium sulfate), filter, and concentrate to give the title compound as a 9:1 mixture of cis/trans diastereomers.

后处理

  1. stirringStir for 1 hour at −78° C.
  2. customSlowly quench the mixture with 0.1 N hydrochloric acid
  3. additionDilute the resulting mixture with ethyl acetate
  4. stirringa saturated aqueous solution of sodium potassium tartrate (Rochelle salt) and stir the biphasic mixture overnight
  5. filtrationFilter the mixture
  6. customto remove
  7. customprecipitates
  8. customseparate the aqueous layer
  9. concentrationSaturate the aqueous phase with sodium chloride
  10. extractionextract with ethyl acetate
  11. additionAdd the
  12. extractionorganic extract to the ethyl acetate solution of the reaction mixture
  13. washwash the resultant mixture with saturated aqueous sodium chloride solution
  14. dry with materialdry (magnesium sulfate)
  15. filtrationfilter
  16. concentrationconcentrate

来源与证据

ORD记录
ord-2df14d6ee4694d99b4c524f669c21778
来源数据集
uspto-grants-2010_06
专利号
US07745438B2

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