Chloromethyl Methyl Ether → 4-Fluoro-3-(methoxymethoxy)benzyl alcohol

HRID 15061

반응식

HRID 15061 반응식
C(N(CC)CC)C.[CH3:8][O:9][CH2:10]Cl.O1CCCC1.[F:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=O)=[CH:20][C:19]=1[OH:27]>C(OCC)(=O)C>[F:17][C:18]1[CH:26]=[CH:25][C:21]([CH2:22][OH:24])=[CH:20][C:19]=1[O:27][CH2:8][O:9][CH3:10]

참가 물질

6

반응물 4

HCID 7864Chloromethyl Methyl EtherHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 5936354-Fluoro-3-hydroxybenzoic acid

생성물 1

HCID 230743114-Fluoro-3-(methoxymethoxy)benzyl alcohol수율 94%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

Triethylamine (1.07 mL) and methoxymethyl chloride (2.24 mL) were added to tetrahydrofuran (10 mL) solution of 4-fluoro-3-hydroxybenzoic acid (1.0 g), and stirred at 0° C. for 2 hours. Ethyl acetate was added to the reaction liquid which then was washed with water and saturated brine, dried over anhydrous magnesium sulfate, the solvent therein was concentrated under reduced pressure and the residue was dissolved in tetrahydrofuran (20 mL). Lithiumaluminium hydride (360 mg) was added, stirred at 0° C. for an hour, ethyl acetate was added and the insoluble matter was removed, followed by washing with saturated brine and drying over anhydrous magnesium sulfate. Concentrating the solvent under reduced pressure, the title compound (1.14 g, 94%) was obtained.

후처리

  1. washthen was washed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationthe solvent therein was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in tetrahydrofuran (20 mL)
  5. additionLithiumaluminium hydride (360 mg) was added
  6. stirringstirred at 0° C. for an hour
  7. additionethyl acetate was added
  8. customthe insoluble matter was removed
  9. washby washing with saturated brine
  10. dry with materialdrying over anhydrous magnesium sulfate
  11. concentrationConcentrating the solvent under reduced pressure

출처 및 근거

ORD 기록
ord-b32e232e6caf496cb7414acd838cedd1
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732456B2

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