Methyl iodide → HCID 68674503、化合物

HRID 1446381ノート

反応式

HRID 1446381 の反応式
[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

参加物

6

反応物 3

HCID 6328Methyl iodideHCID 12836151HCID 12836151、化合物HCID 23665647Potassium tert-butoxide

生成物 1

HCID 68674503HCID 68674503、化合物

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9aec2cb3a18c4be1b1f5327a4f001ec1
出典データセット
uspto-grants-2010_02
特許番号
US07667053B2

反応ノート

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