2,6-Lutidine → 3,5-Difluoro-4-triisopropylsilanyloxybenzaldehyde

HRID 1921873

반응식

HRID 1921873 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:11])[C:9]=1[OH:10])[CH:5]=[O:6].N1C(C)=CC=CC=1C.FC(F)(F)S(O[Si:26]([CH:33]([CH3:35])[CH3:34])([CH:30]([CH3:32])[CH3:31])[CH:27]([CH3:29])[CH3:28])(=O)=O>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:11])[C:9]=1[O:10][Si:26]([CH:33]([CH3:35])[CH3:34])([CH:30]([CH3:32])[CH3:31])[CH:27]([CH3:29])[CH3:28])[CH:5]=[O:6]

참가 물질

5

반응물 3

HCID 79372,6-LutidineHCID 2724529Triisopropylsilyl trifluoromethanesulfonateHCID 101925843,5-Difluoro-4-hydroxybenzaldehyde

생성물 1

HCID 579719203,5-Difluoro-4-triisopropylsilanyloxybenzaldehyde

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

30.0 g (190 mmol) of 3,5-difluoro-4-hydroxybenzaldehyde [CAS 118276-06-5] are dissolved under argon in 600 ml of dichloromethane and, at 0° C., 44.7 g (417 mmol) of 2,6-lutidine are added. Then 87.2 g (284 mmol) of triisopropylsilyl trifluoromethanesulfonate are added dropwise, and the mixture is stirred at RT for 12 h. The solvent is distilled out in vacuo, and the residue is mixed with ammonium chloride solution and stirred for 5 min, and the organic phase is separated off. A further extraction with dichloromethane is carried out, and the organic phases are combined, washed with saturated sodium chloride solution, dried over magnesium sulfate, filtered and washed with dichloromethane, and the solvent is distilled off in vacuo. Chromatography on silica gel 60 (mobile phase: cyclohexane) results in 34.9 g (111 mmol, 58% of theory) of the title compound.

후처리

  1. distillationThe solvent is distilled out in vacuo
  2. additionthe residue is mixed with ammonium chloride solution
  3. stirringstirred for 5 min
  4. customthe organic phase is separated off
  5. extractionA further extraction with dichloromethane
  6. washwashed with saturated sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. washwashed with dichloromethane
  10. distillationthe solvent is distilled off in vacuo

출처 및 근거

ORD 기록
ord-1f19d9fdb0ac4579adbe752fccecb2ee
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173704B2

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