반응 #696700

ord-26d728dca65e4327955dcc14f90f46d3

반응 방정식

B.[Na]
sodium boron hydride
B.[Na]
sodium boron hydride
CCC1Cc2c(cccc2-c2ccccc2)C1=O
2-ethyl-4-phenyl-1-indanone
CC(C)=O
acetone
CCC1Cc2c(-c3ccccc3)cccc2C1O
aimed product
수율 99.3%
CCC1Cc2c(-c3ccccc3)cccc2C1O
2-ethyl-1-hydroxy-4-phenylindan
수율 99.3%

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    기타To a 200-ml three-necked round flask (equipped with a stirrer tip
  2. 2
    workup.ADDITIONAfter the dropwise addition
  3. 3
    기타was elevated to 50° C.
  4. 4
    기타reaction for further 3.5 hours
  5. 5
    기타After the reaction
  6. 6
    온도the mixture was cooled
  7. 7
    농축Then, the reaction mixture was concentrated under reduced pressure
  8. 8
    추출extracted with 50 ml of water and 50 ml of ether
  9. 9
    기타The organic phase was separated
  10. 10
    추출the aqueous phase was extracted twice with 50 ml of ether
  11. 11
    세척The combined organic phases were washed with 100 ml of a saturated saline solution
  12. 12
    건조dried over anhydrous Na2SO4
  13. 13
    workup.DISTILLATIONThen, the solvent was distilled off under reduced pressure

실험 절차

To a 200-ml three-necked round flask (equipped with a stirrer tip, a Dimroth condenser, a dropping funnel and a thermometer) were introduced 0.85 g (22.6 mmol) of sodium boron hydride and 28 ml of ethanol, and then in a nitrogen atmosphere at room temperature, a solution of 10.6 g (45.1 mmol) of 2-ethyl-4-phenyl-1-indanone in 20 ml of ethanol was dropwise added. After the dropwise addition was completed, the temperature was elevated to 50° C. to perform reaction for further 3.5 hours. After the reaction, the mixture was cooled, and acetone was dropwise added to decompose the unreacted sodium boron hydride. Then, the reaction mixture was concentrated under reduced pressure and extracted with 50 ml of water and 50 ml of ether. The organic phase was separated, and the aqueous phase was extracted twice with 50 ml of ether. The combined organic phases were washed with 100 ml of a saturated saline solution and dried over anhydrous Na2SO4. Then, the solvent was distilled off under reduced pressure to obtain 10.67 g of the aimed product (a mixture of two isomers) as a viscous, light yellow liquid (yield: 99%). The properties of the product thus obtained are described below.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US05998039uspto-grants-1999_12