Sodium Iodide → HCID 66759489、化合物

HRID 389544

反応式

HRID 389544 の反応式
[H-].[Na+].C(O[CH:6]([O:10][CH2:11][CH3:12])[C:7]([NH2:9])=[O:8])C.[Br:13][C:14]1[C:18]([CH2:19]Br)=[CH:17][S:16][CH:15]=1.[I-].[Na+].C1[CH2:27][O:26][CH2:25]C1>>[Br:13][C:14]1[C:18]([CH2:19][NH:9][C:7](=[O:8])[CH:6]([O:10][CH2:11][CH3:12])[CH2:25][O:26][CH3:27])=[CH:17][S:16][CH:15]=1

参加物

6

反応物 5

HCID 5238Sodium IodideHCID 8028Tetrahydrofuran2 回HCID 24758Sodium hydrideHCID 1007652,2-DiethoxyacetamideHCID 133547593-Bromo-4-(bromomethyl)thiophene

生成物 1

HCID 66759489HCID 66759489、化合物収率 35%

実験手順

To a suspension of sodium hydride (162 mg, 6.74 mmol) in THF (14 mL, 170 mmol) was added 2,2-diethoxyacetamide (949 mg, 6.45 mmol) in portions, followed by 3-bromo-4-(bromomethyl)thiophene (1.50 g, 5.86 mmol) dropwise as a solution in THF (3 mL) and sodium iodide (87.8 mg, 0.586 mmol). The reaction mixture was heated to reflux for 18 h and then concentrated. The residue was then partitioned between water (40 mL) and ethyl acetate (40 mL). The layers were separated and the aqueous layer was further extracted with ethyl acetate (2×30 mL). The combined organic fractions were dried over sodium sulfate, filtered, and concentrated. Purification by ISCO chromatography (5 to 30% ethyl acetate:heptane) afforded 729 mg (35%) of the title compound as a clear, colorless oil. 1H NMR (400 MHz, CDCl3): δ 7.26-7.29 (m, 1 H), 7.23-7.25 (m, 1 H), 6.99 (br. s., 1 H), 4.83 (s, 1 H), 4.44 (dd, J=6.1, 0.8 Hz, 2 H), 3.21-3.98 (m, 4 H), 1.25 (t, J=6.9 Hz, 6 H); MS (ESI): 322.17, 324.15 [M+H]+; HPLC tR=3.26 min (ZQ3, polar—4 min).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 18 h
  3. concentrationconcentrated
  4. customThe residue was then partitioned between water (40 mL) and ethyl acetate (40 mL)
  5. customThe layers were separated
  6. extractionthe aqueous layer was further extracted with ethyl acetate (2×30 mL)
  7. dry with materialThe combined organic fractions were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by ISCO chromatography (5 to 30% ethyl acetate:heptane)

出典と根拠

ORDレコード
ord-7273c1aef4604380aa8663eaf10690f6
出典データセット
uspto-grants-2013_02
特許番号
US08378104B2

関連ノート

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