Ammonium Chloride → 1-(2-Phenylquinolin-7-yl)-ethanol

HRID 230242

반응식

HRID 230242 반응식
[CH3:1][Mg+].[Br-].[C:4]1([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][C:14]([CH:20]=[O:21])=[CH:15][CH:16]=3)[N:11]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH4+].[Cl-]>C1COCC1>[C:4]1([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][C:14]([CH:20]([OH:21])[CH3:1])=[CH:15][CH:16]=3)[N:11]=2)[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 468355462-Phenylquinoline-7-carbaldehydeHCID 178418689HCID 178418689, 화합물

생성물 1

HCID 577623971-(2-Phenylquinolin-7-yl)-ethanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Into the THF (50 ml) solution of MeMgBr (3M in Et2O, 5.6 mL, 1.5 eq.) was added dropwise the THF (40 ml) solution of 2-phenylquinoline-7-carbaldehyde (2625 mg, 11.25 mmol) under N2 at rt over 20 min. After stirring at rt for 3 h, the reaction mixture was treated with saturated aqueous NH4Cl solution (100 ml), and the organic phase was separated. The aqueous phase was extracted with EtOAc (2×100 ml). The combined organic phases were then washed with H2O (2×100 ml) and brine (100 ml), dried over MgSO4, filtered and concentrated to give the title compound as brown oil. The crude material was used for the next step without further purification. 1H NMR (CDCl3, 400 MHz): δ=1.60-1.62 (d, 3H, J=6.4 Hz), 2.08 (brs, 1H), 5.11-5.14 (m, 1H), 7.44-7.60 (m, 4H), 7.81-7.83 (d, 1H, J=8.4 Hz), 7.85-7.87 (d, 1H, J=8.4 Hz), 8.13-8.17 (m, 3H), 8.19-8.21 (d, 1H, J=8.4 Hz). MS (ES+): 250.3 [MH+]. HPLC: tR=2.9 min (MicromassZQ, polar—5 min).

후처리

  1. customthe organic phase was separated
  2. extractionThe aqueous phase was extracted with EtOAc (2×100 ml)
  3. washThe combined organic phases were then washed with H2O (2×100 ml) and brine (100 ml)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-255d454a516745e7bff7c699d45f2129
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07566721B2

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