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

HRID 22929

반응식

HRID 22929 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매2회HCID 6344Dichloromethane용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-404384f4293543e2a362626d6c1a5a64
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06849649B2

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