Methyl iodide → HCID 68674503, 화합물

HRID 1446381노트

반응식

HRID 1446381 반응식
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH:2]1[C:10]([O:12][CH3:13])=[O:11].CI.[CH3:16]C(C)([O-])C.[K+]>O1CCCC1.C(OCC)(=O)C>[CH3:16][C:2]1([C:10]([O:12][CH3:13])=[O:11])[CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[O:1]1

참가 물질

6

반응물 3

HCID 6328Methyl iodideHCID 12836151HCID 12836151, 화합물HCID 23665647Potassium tert-butoxide

생성물 1

HCID 68674503HCID 68674503, 화합물

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of methyl 2,3-dihydrobenzofuran-2-carboxylate (Step A, 1.0 g, 5.5 mmol) and methyl iodide (1.8 mL, 28 mmol) in 20 mL of anhydrous tetrahydrofuran at −78° C. was added potassium tert-butoxide (1 M in tetrahydrofuran, 8.4 mL, 8.4 mmol). The reaction was allowed to warm to room temperature overnight, and the resulting mixture was diluted with ethyl acetate (100 mL), washed with aqueous saturated ammonium chloride (100 mL) and water, dried over anhydrous sodium sulfate, filtered and concentrated to dryness. The residue was purified by flash column chromatography eluted with 2-5% ethyl acetate in hexane to give the title compound. 1H NMR (500 MHz, CD3OD): δ 7.16 (d, 1H), 7.12 (t, 1H), 6.86 (t, 1H), 6.76 (d, 1H), 3.75 (s, 3H), 3.58 (d, 1H), 3.17 (d, 1H), 1.66 (s, 3H).

후처리

  1. washwashed with aqueous saturated ammonium chloride (100 mL) and water
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customThe residue was purified by flash column chromatography
  6. washeluted with 2-5% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-9aec2cb3a18c4be1b1f5327a4f001ec1
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07667053B2

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