Coumaranone → Benzofuran-3-acetonitrile

HRID 431785

반응식

HRID 431785 반응식
[H-].[Na+].CCOP(OCC)([CH2:8][C:9]#[N:10])=O.[O:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16](=O)[CH2:15]1>C1COCC1.CCOC(C)=O.O>[O:14]1[C:22]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:16]([CH2:8][C:9]#[N:10])=[CH:15]1

참가 물질

7

반응물 3

HCID 23556CoumaranoneHCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonate

생성물 1

HCID 2769401Benzofuran-3-acetonitrile수율 91%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

Sodium hydride (268 mg, 6.7 mmol) was slurried in dry THF (10 ml) at 0° C. under nitrogen and diethyl cyanomethyl phosphonate (1.1 ml, 6.7 mmol) added dropwise and the whole stirred for 45 min. 3-Coumaranone (Lancaster) (900 mg, 6.7 mmol) was then added dropwise and the whole stirred at room temperature for 45 min. The reaction was diluted with EtOAc (15 ml) and water (15 ml), and the organic layer was then separated, dried (MgSO4) and evaporated and the residue flash chromatographed using 0-5% EtOAc in pentane to give the title product (940 mg, 91%); 1HNMR (400 MHz, CDCl3) δ: 3.77 (s, 2H), 7.25-7.40 (m, 2H), 7.52 (dd, 1H), 7.58 (dd, 1H), 7.67 (s, 1H); LRMS: M+NH4+, 175. (TS+).

후처리

  1. stirringthe whole stirred at room temperature for 45 min
  2. customthe organic layer was then separated
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customthe residue flash chromatographed

출처 및 근거

ORD 기록
ord-dcf6a7a44a134677af4f3871218f3b28
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06660756B2

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