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

HRID 1438158ノート

反応式

HRID 1438158 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 579428023-Ethoxy-5-ethyl-2-fluorobenzaldehyde収率 100%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-5d5db87ccb1747ba9fae5a82e0bda9b6
出典データセット
uspto-grants-2009_11
特許番号
US07622585B2

反応ノート

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