Water → 3,4-Dimethoxy-6-(4-pyridyl) hydroxymethylbenzaldehyde dimethylacetal

HRID 1740651

반응식

HRID 1740651 반응식
[CH3:1][O:2][CH:3]([O:15][CH3:16])[C:4]1[C:9](Br)=[CH:8][C:7]([O:11][CH3:12])=[C:6]([O:13][CH3:14])[CH:5]=1.C([Li])CCC.C([C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1)=O.O.[O:31]1CCC[CH2:32]1>CCCCCC.C(OCC)(=O)C>[CH3:1][O:2][CH:3]([O:15][CH3:16])[C:4]1[C:9]([C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)=[CH:8][C:7]([O:11][CH3:12])=[C:6]([O:13][CH3:14])[C:5]=1[CH2:32][OH:31]

참가 물질

8

반응물 5

HCID 962WaterHCID 8028Tetrahydrofuran2회HCID 133894-PyridinecarboxaldehydeHCID 110771461-Bromo-2-(dimethoxymethyl)-4,5-dimethoxybenzeneHCID 178418339Butyllithium

생성물 1

HCID 220073783,4-Dimethoxy-6-(4-pyridyl) hydroxymethylbenzaldehyde dimethylacetal

시약·촉매·용매 2

HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 6-bromo-3,4-dimethoxybenzaldehyde dimethyl acetal (20 ml) in tetrahydrofuran (100 ml) is cooled to -60° C., and thereto is added dropwise a 1.6 M solution of n-butyl lithium in hexane (45.1 ml) over a period of 20 minutes under nitrogen atmosphere. The mixture is reacted at the same temperature for 30 minutes, and thereto is added dropwise a solution of 4-formylpyridine (7.36 g) in tetrahydrofuran (50 ml) over a period of 20 minutes. The reaction mixture is reacted for one hour, and thereto are added water and ethyl acetate (200 ml). The ethyl acetate layer is separated, washed, dried, and concentrated under reduced pressure to remove the ethyl acetate to give 3,4-dimethoxy-6-(4-pyridyl)hydroxymethylbenzaldehyde dimethyl acetal (15.4 g).

후처리

  1. customThe mixture is reacted at the same temperature for 30 minutes
  2. customThe reaction mixture is reacted for one hour
  3. customThe ethyl acetate layer is separated
  4. washwashed
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customto remove the ethyl acetate

출처 및 근거

ORD 기록
ord-be86f9b8e25c439380ac94cc637eaf5e
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05969140

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