(E)-N-methoxy-N-methyl-3-(3-cyclopentoxy-4-methoxyphenyl)-prop-2-enamide → (E)-5-(3-cyclopentoxy-4-methoxyphenyl)-pent-4-en-3-one

HRID 1377755ノート

反応式

HRID 1377755 の反応式
CON(C)[C:4](=[O:21])/[CH:5]=[CH:6]/[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([O:15][CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:8]=1.[CH3:23][CH2:24][Mg]Br>C1COCC1.CCOCC>[CH:16]1([O:15][C:9]2[CH:8]=[C:7](/[CH:6]=[CH:5]/[C:4](=[O:21])[CH2:23][CH3:24])[CH:12]=[CH:11][C:10]=2[O:13][CH3:14])[CH2:17][CH2:18][CH2:19][CH2:20]1

参加物

5

反応物 2

HCID 21193737(E)-N-methoxy-N-methyl-3-(3-cyclopentoxy-4-methoxyphenyl)-prop-2-enamideHCID 178418443HCID 178418443、化合物

生成物 1

HCID 22915235(E)-5-(3-cyclopentoxy-4-methoxyphenyl)-pent-4-en-3-one収率 34%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (E)-N-methoxy-N-methyl-3-(3-cyclopentoxy-4-methoxyphenyl)-prop-2-enamide (1.33 g, 4.36 mmol) in 8.0 mL of THF cooled to 0° C. was added CH3CH2MgBr (9 mL of 1.0M THF solution). The resulting solution was stirred for 30 min, diluted with ether and transferred to a separatory funnel. After washing with H2O, 1M H3PO4, and brine, the organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. Silica gel chromatography (4:1, hexanes:ethyl acetate) provided (E)-5-(3-cyclopentoxy-4-methoxyphenyl)-pent-4-en-3-one as a white solid (400 mg, 34%). 1H-NMR (300 MHz): δ 1.17 (t, 3, J=7.6), 2.69 (q, 2, J=7.3), 3.89 (s, 3), 6.59 (d, 1, J=16), 7.50 (d, 1, J=16). Anal. Calcd for C17H22O3 : C, 74.42; H, 8.08. Found: C, 74.52; H, 8.13.

後処理

  1. customtransferred to a separatory funnel
  2. washAfter washing with H2O, 1M H3PO4, and brine
  3. dry with materialthe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-9456f690dcc84d1dbd63ce1bc1cc1561
出典データセット
uspto-grants-1997_09
特許番号
US05665754

反応ノート

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