Tetrahydrofuran → 4-Fluoro-N-[2-(5-methyl-2-furanyl)ethyl]benzamide

HRID 1441797

反応式

HRID 1441797 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]C(Cl)=O)=[CH:4][CH:3]=1.[CH3:12][C:13]1[O:17][C:16]([CH2:18][CH2:19][NH2:20])=[CH:15][CH:14]=1.CCN(CC)CC.C1C[O:31]CC1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:20][CH2:19][CH2:18][C:16]2[O:17][C:13]([CH3:12])=[CH:14][CH:15]=2)=[O:31])=[CH:6][CH:7]=1

参加物

5

反応物 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 37449884-Fluorophenylacetyl chlorideHCID 149337782-(5-Methylfuran-2-yl)ethan-1-amine

生成物 1

HCID 218748464-Fluoro-N-[2-(5-methyl-2-furanyl)ethyl]benzamide収率 95%

実験手順

4-Fluorophenylacetyl chloride (0.290 mL, 2.44 mmol) was added dropwise to a solution of β-(5-methyl-2-furanyl)ethanamine (300 mg, 2.44 mmol, made according to the procedure of Yur'ev et al. J. Gen. Chem. USSR (Engl. Transl.) 33, 3444-8 (1963)) in THF (2.5 mL) at rt, followed by the dropwise addition of Et3N (0.340 mL, 2.44 mmol). Once the starting material was consumed, as was evident by HPLC, the reaction was quenched with H2O and extracted with CH2Cl2. The combined organic layers were dried over MgSO4 and concentrated under reduced pressure. Purification by flash chromatography on silica gel eluting with a gradient of 0-50% EtOAc/hexane gave 523 mg (95%) of compound 237A as a white solid. HPLC: 99% at 2.84 min (retention time) (Phenomenex-prime S5-C18 column 4.6×50 mm eluting with 10-90% aqueous methanol over 4 minutes containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm). MS (ES): m/z 248.15 [M+H]+.

後処理

  1. customOnce the starting material was consumed
  2. customthe reaction was quenched with H2O
  3. extractionextracted with CH2Cl2
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customPurification by flash chromatography on silica gel eluting with a gradient of 0-50% EtOAc/hexane

出典と根拠

ORDレコード
ord-0a07f5257e424f85bdeaaf3a28935b54
出典データセット
uspto-grants-2010_02
特許番号
US07655689B2

関連ノート

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