Ethyl Acetate → HCID 86668040, 화합물

HRID 538328노트

반응식

HRID 538328 반응식
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.[Li+].CC([N-]C(C)C)C.[CH2:17]([O:19][C:20](Cl)=[O:21])[CH3:18].[NH4+].[Cl-].[C:25]([O:28][CH2:29][CH3:30])(=[O:27])C>C1COCC1>[CH2:17]([O:19][C:20](=[O:21])[CH:8]([C:6]1[CH:5]=[CH:4][N:3]=[C:2]([Br:1])[CH:7]=1)[C:25]([O:28][CH2:29][CH3:30])=[O:27])[CH3:18]

참가 물질

7

반응물 5

HCID 8857Ethyl AcetateHCID 10928Ethyl chloroformateHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 27340872-Bromo-4-methylpyridine

생성물 1

HCID 86668040HCID 86668040, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

2-Bromo-4-methyl pyridine (70.0 g, 407 mmol) was added drop wise to a cooled (−78° C.) solution of LDA (2.0 M in toluene/THF/ethyl benzene, 610.4 ml, 1.22 mol) in dry THF (600 ml) for 30 min. ethylchloroformate (132.3 g, 1.22 mol) was added to the resultant reaction mixture with addition funnel at −78° C. and stirring continued for 90 min. Reaction mixture was treated with saturated NH4Cl solution and worked up with ethyl acetate by washing with water, brine followed by drying over anhy. Na2SO4. Organic layer was concentrated under reduced pressure to obtain crude product which was purified by column chromatography with 10% ethyl acetate in Hexane to furnish title compound as a brown color oily liquid. Yield: 115.0 g (89%). TLC (10% ethyl acetate in hexane) Rf=0.15; LCMS: RtH8=1.475 [M+1]+=315.8 and 317.8; HPLC RtH9=7.30 min (86.7%); 1H NMR (400 MHz, CDCl3) b 8.38 (d, 1H), 7.56 (t, 1H), 7.34 (dd, 1H), 4.55 (s, 1H), 4.29-4.18 (m, 4H), 1.28 (t, 6H).

후처리

  1. additionwas added to the resultant
  2. customreaction mixture
  3. additionwith addition funnel at −78° C.
  4. customReaction mixture
  5. washby washing with water, brine
  6. customby drying over anhy
  7. concentrationOrganic layer was concentrated under reduced pressure
  8. customto obtain crude product which
  9. customwas purified by column chromatography with 10% ethyl acetate in Hexane

출처 및 근거

ORD 기록
ord-f91ca58f0e4f41f5983dde8220895431
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865712B2

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