Citric Acid → HCID 14793480, compound

HRID 358937Notes

Reaction equation

HRID 358937 reaction equation
[C:1]([C:3]([CH3:12])([CH2:9][CH2:10][CH3:11])[C:4](OCC)=[O:5])#[N:2].[Cl-].[Li+].[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1.C(O)C>[C:1]([C:3]([CH3:12])([CH2:9][CH2:10][CH3:11])[CH2:4][OH:5])#[N:2]

Participants

7

Reactant 4

HCID 311Citric AcidHCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 15099993HCID 15099993, compound

Product 1

HCID 14793480HCID 14793480, compoundYield 78.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2.28 g(13.5 mM) of (-)-ethyl 2-cyano-2-methylpentanoate in 22 ml of dry tetrahydrofuran was added dropwise to a mixture of 1.14 mg (27.0 mM) of anhydrous lithium chloride and 1.02 mg (27.0 mM) of sodium borohydride under stirring at room temperature. Then, 44 ml of dry ethanol was added thereto, followed by 16 hours of reaction at room temperature. After the reaction, while the reaction mixture was cooled on an ice bath, 10% citric acid was added until the pH reached 4. A white solid recipitated at this time was separated by filtration, and the solvent was removed from the filtrate by reduced pressure distillation. Then, 5 ml of distilled water was added to the product, followed by extraction with dichloromethane. The resultant organic layer was dried on sodium sulfate, followed by distilling-off of the solvent under reduced pressure and further distillation to obtain 9.35 mg(10.6 mM) of (+)-2-cyano-2-methylpentanol. Yield:78.7%, b.p. 110° C.; [α]D -0.9 degree, [α]435 -1.6 degree (c1, CH2Cl2).

Workup

  1. customfollowed by 16 hours of reaction at room temperature
  2. customAfter the reaction
  3. temperaturewhile the reaction mixture was cooled on an ice bath
  4. customwas separated by filtration
  5. customthe solvent was removed from the filtrate by reduced pressure distillation
  6. additionThen, 5 ml of distilled water was added to the product
  7. extractionfollowed by extraction with dichloromethane
  8. customThe resultant organic layer was dried on sodium sulfate
  9. distillationfollowed by distilling-off of the solvent under reduced pressure and further distillation

Sources & evidence

ORD record
ord-f88bda3174744e6f87f63a967acff330
Source dataset
uspto-grants-1991_03
Patent number
US04999130

Reaction notes

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