Lithium diisopropylamide → HCID 22490963, 화합물

HRID 2180599노트

반응식

HRID 2180599 반응식
[Br:1][C:2]1[C:11]2[C:10]([CH3:13])([CH3:12])[CH2:9][CH:8]=[C:7]([CH:14]([CH3:16])[CH3:15])[C:6]=2[CH:5]=[C:4]([C:17](=[O:19])[CH3:18])[C:3]=1[O:20][CH2:21][CH3:22].[CH:23]([N-]C(C)C)(C)C.[Li+]>C1COCC1>[Br:1][C:2]1[C:11]2[C:10]([CH3:13])([CH3:12])[CH2:9][CH:8]=[C:7]([CH:14]([CH3:16])[CH3:15])[C:6]=2[CH:5]=[C:4]([C:17](=[O:19])[CH2:18][CH3:23])[C:3]=1[O:20][CH2:21][CH3:22]

참가 물질

4

반응물 2

HCID 2724682Lithium diisopropylamideHCID 22490930HCID 22490930, 화합물

생성물 1

HCID 22490963HCID 22490963, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

To a solution of 1-(4-bromo-3-ethoxy-8-isopropyl-5,5-dimethyl-5,6-dihydro-naphthalen-2-yl)-ethanone (Compound A-109, 1.75 g, 4.81 mmol) in THF (33 mL) at −78° C. was added lithium diisopropylamide (1.5 M in cyclohexane, 3.85 mL, 5.78 mmol). The bath was removed and the mixture was stirred for 2.5 h. The mixture was cooled to −78° C. again and methyl iodide was added. The mixture was stirred at room temperature for 16 h, quenched with saturated ammonium chloride, and extracted with diethyl ether. The combined ethereal layers were washed with water, brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified by flash chromatography (silica gel, 2% ethyl acetate in hexanes) followed by HPLC (normal phase, 2% ethyl acetate in hexanes) to give the title compound as clear oil.

후처리

  1. customThe bath was removed
  2. additionmethyl iodide was added
  3. stirringThe mixture was stirred at room temperature for 16 h
  4. customquenched with saturated ammonium chloride
  5. extractionextracted with diethyl ether
  6. washThe combined ethereal layers were washed with water, brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude residue was purified by flash chromatography (silica gel, 2% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-87e9310f14634225a98a2a9c6779e55c
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06887896B1

반응 노트

불러오는 중…