Methanol → HCID 20066028、化合物

HRID 2265115ノート

反応式

HRID 2265115 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 20066028HCID 20066028、化合物収率 96%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 962Water溶媒

反応条件

温度
70 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-bf93564a0c864673968bc48772fe99fa
出典データセット
uspto-grants-2010_12
特許番号
US07855300B2

反応ノート

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