Dimethylformamide → (3-Ethylphenyl)methanol

HRID 324456

반응식

HRID 324456 반응식
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][CH3:14])[CH:8]=1.CN(C)[CH:17]=[O:18]>O1CCCC1>[CH2:13]([C:9]1[CH:8]=[C:7]([CH2:17][OH:18])[CH:12]=[CH:11][CH:10]=1)[CH3:14]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 123170Benzene, 1-bromo-3-ethyl-HCID 178418339Butyllithium

생성물 1

HCID 104659(3-Ethylphenyl)methanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

n-Butyllithium (34 ml of a 2.5M solution in hexanes) was added to a solution of 1-bromo-3-ethylbenzene (15 g) in tetrahydrofuran (320 ml) at −78° C. After 1 hour N,N-dimethylformamide (15 ml) was added. The mixture was stirred at −78° C. for 1 hour and allowed to warm to room temperature. The mixture was quenched with aqueous ammonium chloride and partitioned between ethyl acetate and water. The organic phase was dried (MgSO4) and evaporated. The residue was dissolved in methanol (250 ml) and treated with sodium borohydride (1.51 g) portionwise. The mixture was stirred at room temperature for 16 hours, quenched with 2M HCl (100 ml) and stirred for 4 hours. The mixture was concentrated under reduced pressure and the residue partitioned between ethyl acetate and 2M HCl. The organic phase was dried (MgSO4), evaporated and the residue purified by chromatography eluting with 5-10% ethyl acetate in isohexane.

후처리

  1. temperatureto warm to room temperature
  2. customThe mixture was quenched with aqueous ammonium chloride
  3. custompartitioned between ethyl acetate and water
  4. dry with materialThe organic phase was dried (MgSO4)
  5. customevaporated
  6. dissolutionThe residue was dissolved in methanol (250 ml)
  7. additiontreated with sodium borohydride (1.51 g) portionwise
  8. stirringThe mixture was stirred at room temperature for 16 hours
  9. customquenched with 2M HCl (100 ml)
  10. stirringstirred for 4 hours
  11. concentrationThe mixture was concentrated under reduced pressure
  12. customthe residue partitioned between ethyl acetate and 2M HCl
  13. dry with materialThe organic phase was dried (MgSO4)
  14. customevaporated
  15. customthe residue purified by chromatography
  16. washeluting with 5-10% ethyl acetate in isohexane

출처 및 근거

ORD 기록
ord-7614c6145c424c9396a8ab177d39f1fb
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06218376B1

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