Iodoethane → 3-Ethoxy-5-ethyl-2-fluorobenzaldehyde

HRID 1438158노트

반응식

HRID 1438158 반응식
[Si]([O:8][C:9]1[C:10]([F:19])=[C:11]([CH:14]=[C:15]([CH2:17][CH3:18])[CH:16]=1)[CH:12]=[O:13])(C(C)(C)C)(C)C.[F-].[K+].I[CH2:23][CH3:24]>CN(C=O)C.CCOC(C)=O>[CH2:23]([O:8][C:9]1[C:10]([F:19])=[C:11]([CH:14]=[C:15]([CH2:17][CH3:18])[CH:16]=1)[CH:12]=[O:13])[CH3:24]

참가 물질

6

반응물 3

HCID 6340IodoethaneHCID 522689Potassium FluorideHCID 598380723-{[tert-Butyl(dimethyl)silyl]oxy}-5-ethyl-2-fluorobenzaldehyde

생성물 1

HCID 579428023-Ethoxy-5-ethyl-2-fluorobenzaldehyde수율 100%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To 118C (244 mg, 0.87 mmol) in DMF (2.0 mL) was added potassium fluoride (100 mg) and iodoethane (0.13 mL). The mixture was stirred at rt overnight. It was diluted with EtOAc and the organic extracts were washed with brine and dried. The crude product was purified by column chromatography to give 118D (158 mg, 100% yield) as an oil. 1H NMR (400 MHz, CDCl3) δ ppm 1.22 (t, J=7.69 Hz, 3H) 1.46 (t, J=7.03 Hz, 3H) 2.62 (q, J=7.47 Hz, 2H) 4.13 (q, J=7.03 Hz, 2H) 7.02 (dd, J=7.91, 2.20 Hz, 1H) 7.22 (dd, J=5.27, 2.20 Hz, 1H) 10.35 (s, 1H).

후처리

  1. washthe organic extracts were washed with brine
  2. customdried
  3. customThe crude product was purified by column chromatography

출처 및 근거

ORD 기록
ord-5d5db87ccb1747ba9fae5a82e0bda9b6
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07622585B2

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