Acetone → 4-(2,3-Dihydro-1-benzofuran-5-yl)but-3-en-2-one

HRID 22929

反応式

HRID 22929 の反応式
[O:1]1[CH2:5][CH2:4][C:3]2[CH:6]=[C:7]([CH:10]=O)[CH:8]=[CH:9][C:2]1=2.[CH3:12][C:13]([CH3:15])=[O:14].[OH-].[Na+].Cl>C(Cl)Cl.O>[O:1]1[C:2]2[CH:9]=[CH:8][C:7](/[CH:10]=[CH:12]/[C:13](=[O:14])[CH3:15])=[CH:6][C:3]=2[CH2:4][CH2:5]1

参加物

7

反応物 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 7359012,3-Dihydrobenzofuran-5-carboxaldehyde

生成物 1

HCID 225923854-(2,3-Dihydro-1-benzofuran-5-yl)but-3-en-2-one収率 84%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 6344Dichloromethane溶媒

実験手順

2,3-Dihydrobenzo[b]furan-5-carboxaldehyde (Aldrich Chemicals) (2 g, 13.5 mmol), acetone (2.73 ml, 37.1 mmol), water (1.35 ml) and 10% NaOH (aq.) (0.34 ml) were added together and the whole stirred at room temperature for 16 h. The yellow solid was redissolved in approx. 15 ml DCM and 2N HCl added to achieve a solution of pH2. Water (10 ml) was added and the organic layer was extracted with DCM (2×20 ml). The aqueous layers were separated, and re-extracted with DCM (2×15 ml). The combined organics were dried (MgSO4) and concentrated in vacuo to a yellow solid which was purified by column chromatography using 15-30% EtOAc in pentane as eluant to provide the title product (2.13 g, 84%); 1HNMR (400 MHz, CDCl3) δ: 2.3 (s, 3H), 3.2 (t, 2H), 4.6 (t, 2H), 6.5 (d, 1H), 6.75 (d, 1H), 7.3 (d, 1H), 7.4 (s, 1H), 7.45 (d, 1H); LRMS: M+H, 189. (ES+).

後処理

  1. extractionthe organic layer was extracted with DCM (2×20 ml)
  2. customThe aqueous layers were separated
  3. extractionre-extracted with DCM (2×15 ml)
  4. dry with materialThe combined organics were dried (MgSO4)
  5. concentrationconcentrated in vacuo to a yellow solid which
  6. customwas purified by column chromatography

出典と根拠

ORDレコード
ord-404384f4293543e2a362626d6c1a5a64
出典データセット
uspto-grants-2005_02
特許番号
US06849649B2

関連ノート

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