Methanol → HCID 20066028, 화합물

HRID 2265115노트

반응식

HRID 2265115 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](/[C:10](/[CH3:17])=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][CH:5]=1)([O-])=O.[Cl-].[NH4+].O1CCCC1.CO>[Fe].O>[NH2:1][C:4]1[CH:5]=[CH:6][C:7](/[C:10](/[CH3:17])=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8][CH:9]=1

참가 물질

7

반응물 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 614540480854-57-5

생성물 1

HCID 20066028HCID 20066028, 화합물수율 96%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 962Water용매

반응 조건

온도
70 °C

실험 절차

Compound 19a (929 mg), iron powder (1.97 g), and ammonium chloride (436 mg) were added to a mixed solution of tetrahydrofuran (4 ml), methanol (4 ml), and water (4 ml). The obtained mixture was stirred at 70° C. for 3.5 hours. The mixture was allowed to cool and then filtered. The filtrate was separated with ethyl acetate and water. The organic layer was sequentially washed twice with water and once with a saturated sodium chloride solution, and then dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by column chromatography (17%-33% ethyl acetate/n-hexane) to obtain Compound 19b (757 mg, 96%) as an orange solid. 1H-NMR (CDCl3) δ7.35 (2H, d, J=8.7 Hz), 6.65 (2H, d, J=8.7 Hz), 6.09 (1H, s), 4.19 (2H, q, J=7.1 Hz), 3.85 (2H, brs), 2.54 (3H, s), 1.30 (3H, t, J=7.1 Hz).

후처리

  1. temperatureto cool
  2. filtrationfiltered
  3. customThe filtrate was separated with ethyl acetate and water
  4. washThe organic layer was sequentially washed twice with water and once with a saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off
  7. customthe residue was purified by column chromatography (17%-33% ethyl acetate/n-hexane)

출처 및 근거

ORD 기록
ord-bf93564a0c864673968bc48772fe99fa
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07855300B2

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