Hydrochloric Acid → HCID 12082058, compound

HRID 1760354Notes

Reaction equation

HRID 1760354 reaction equation
C([Li])CCC.[O:6]1[CH2:10][CH2:9][CH2:8][C@@H:7]1[C:11]#N.Cl.[O:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1>CCCCCC.O>[O:14]1[CH2:18][CH2:17][CH2:16][C@@H:15]1[C:10](=[O:6])[CH2:9][CH2:8][CH2:7][CH3:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 7204860(S)-TETRAHYDROFURAN-2-CARBONITRILEHCID 178418339Butyllithium

Product 1

HCID 12082058HCID 12082058, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

A 1 L reactor at a temperature of 0° C. was added with 0.4 L of 1.6 M n-butyllithium in n-hexane, to which 13.5 g of (R)-2-tetrahydrofuran nitrile as previously obtained, in 0.07 L of tetrahydrofuran was slowly added dropwise. As such, the reaction was carried out for 1 hour with stirring, while the temperature within the reactor was controlled below 15° C. Next, the resulting solution was added dropwise to 65 g of concentrated hydrochloric acid in 0.4 L of water, while the temperature of the reaction was controlled below 25° C. Thereafter, the extraction was conducted by use of ethylacetate, followed by removing the solvent therein under reduced pressure, and the remainder was vacuum distilled off to produce 19.6 g of (R)-1-(2-tetrahydrofuranyl)-1-pentanone having an optical purity of 98.5% ee.

Workup

  1. additionwas slowly added dropwise
  2. customwas controlled below 15° C
  3. customwas controlled below 25° C
  4. extractionThereafter, the extraction
  5. customby removing the solvent
  6. distillationdistilled off

Sources & evidence

ORD record
ord-80b99ff642254f31a5c535c8dde0bc85
Source dataset
uspto-grants-2005_01
Patent number
US06841688B2

Reaction notes

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