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HRID1905072

反应详情

EQUATION

反应方程式

HRID 1905072 的结构方程式

REACTANTS

反应物

3
结构：CC(C)(C=O)CCC#N
HCID80231

4-Formyl-4-methylvaleronitrile

C7H11NO

结构：[BH4-].[Na+]
HCID4311764

Sodium borohydride (Na(BH4))

H4BNa

结构：CCOC(C)=O.ClCCl
HCID21226138

未命名化合物

PRODUCTS

生成物

1
结构：CC(C)(CO)CCC#N
HCID91357

5-Hydroxy-4,4-dimethylvaleronitrile

C7H13NO

AUXILIARIES

试剂、催化剂与溶剂

2
结构：O=P(O)(O)O.[O]=[Mo](=[O])=[O].[O]=[Mo](=[O])=[O].[O]=[Mo](=[O])=[O].[O]=[Mo](=[O])=[O].[O]=[Mo](=[O])=[O].[O]=[Mo](=[O])=[O].[O]=[Mo](=[O])=[O].[O]=[Mo](=[O])=[O].[O]=[Mo](=[O])=[O].[O]=[Mo](=[O])=[O].[O]=[Mo](=[O])=[O].[O]=[Mo](=[O])=[O]
催化剂HCID11251951

Molybdenum, trioxo-, compd. with phosphoric acid (12:1

H3Mo12O40P

结构：CO
溶剂HCID887

Methanol

CH4O

PROCEDURE

实验过程

To a solution of 47 g (0.376 mmol) of 4,4-dimethyl-5-oxovaleronitrile in 350 mL of methanol, cooled to 0° C. (ice bath), was added, with vigorous stirring and over 15-20 min., 7.9 g (0.209 mmol; 2.22 hydride equiv.) of NaBH4. After the addition was completed, the solution was stirred an additional 30 min. at 0° C. before removing the solvent in vacuo (aspirator . To the residue was added CH2Cl2 followed by careful addition of H2O, and finally 1.2N HCl until pH=1-2 was obtained. The layers were separated and the aqueous one extracted twice (CH2Cl2), saturated with NaCl and extracted again three times with CH2Cl2. After drying the combined organic layers over Na2SO4 and removing the solvent under vacuum (aspirator) 47.7 g (95%) of the title compound, sufficiently pure for the next step, was obtained as a faint yellow oil. TLC: (Silica) Rf =0.26 (ethyl acetate dichloromethane 1:9), detection with molybdophosphoric acid (yellow spot on blue-green).

WORKUP

后处理

  1. additionwas added
  2. additionAfter the addition
  3. stirringthe solution was stirred an additional 30 min. at 0° C.
  4. custombefore removing the solvent in vacuo (aspirator
  5. additionTo the residue was added CH2Cl2
  6. additionfollowed by careful addition of H2O, and finally 1.2N HCl until pH=1-2
  7. customwas obtained
  8. customThe layers were separated
  9. extractionthe aqueous one extracted twice (CH2Cl2)
  10. extractionsaturated with NaCl and extracted again three times with CH2Cl2
  11. dry with materialAfter drying the combined organic layers over Na2SO4
  12. customremoving the solvent under vacuum (aspirator) 47.7 g (95%) of the title compound
  13. customsufficiently pure for the next step, was obtained as a faint yellow oil