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

HRID 723661

반응식

HRID 723661 반응식
[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

참가 물질

5

반응물 4

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

생성물 1

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

실험 절차

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 1090% 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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-2dca0ba2cdac47c0a7d8c908db8f5311
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07141578B2

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