p-Toluenesulfonic acid → 2-Fluoro-3-(2-hydroxyethoxymethyl)-5-methoxybenzaldehyde

HRID 1161580노트

반응식

HRID 1161580 반응식
C[O:2][CH:3](OC)[C:4]1[C:5]([F:23])=[C:6]([CH:18]=[C:19]([O:21][CH3:22])[CH:20]=1)[CH2:7][O:8][CH2:9][CH2:10][O:11]C1CCCCO1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1COCC1.O>[F:23][C:5]1[C:6]([CH2:7][O:8][CH2:9][CH2:10][OH:11])=[CH:18][C:19]([O:21][CH3:22])=[CH:20][C:4]=1[CH:3]=[O:2]

참가 물질

5

반응물 2

HCID 6101p-Toluenesulfonic acidHCID 595174642-[2-(3-Dimethoxymethyl-2-fluoro-5-methoxybenzyloxy]ethoxy]tetrahydropyran

생성물 1

HCID 595168732-Fluoro-3-(2-hydroxyethoxymethyl)-5-methoxybenzaldehyde수율 46.3%

시약·촉매·용매 2

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

실험 절차

2-[2-(3-Dimethoxymethyl-2-fluoro-5-methoxybenzyloxy]ethoxy]tetrahydropyran (1.035 g) was dissolved in 10 ml of THF and 3 ml of water, and 1 g of p-toluenesulfonic acid was added thereto. The resulting mixture was stirred at room temperature overnight, and then water was added thereto. The mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The desiccating agent was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (heptane-ethyl acetate) to give the title compound (305 mg).

후처리

  1. extractionThe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customThe desiccating agent was removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (heptane-ethyl acetate)

출처 및 근거

ORD 기록
ord-44c6ed68584a4ab982010c1ac8f88781
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07816522B2

반응 노트

불러오는 중…