Sodium Iodide → HCID 53788388、化合物

HRID 1432883ノート

反応式

HRID 1432883 の反応式
C([O-])(O)=O.[Na+].[Na+].[I-].Br[C:9]1[S:13][C:12]([Cl:14])=[CH:11][CH:10]=1.[CH2:15]([OH:18])[CH:16]=[CH2:17]>CN(P(N(C)C)(N(C)C)=O)C.CCOCC.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:14][C:12]1[S:13][C:9]([CH2:17][CH2:16][CH:15]=[O:18])=[CH:10][CH:11]=1

参加物

8

反応物 4

HCID 5238Sodium IodideHCID 7858Allyl AlcoholHCID 761332-Bromo-5-chlorothiopheneHCID 516892Sodium Bicarbonate

生成物 1

HCID 53788388HCID 53788388、化合物収率 20.4%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 3283Diethyl Ether溶媒HCID 12679Hexamethylphosphoramide溶媒

反応条件

温度
90 °C

実験手順

To a mixture of Pd(OAc)2 (0.12 g, 0.53 mmol), NaHCO3 (0.52 g, 6.19 mmol) and NaI (0.28 g, 1.87 mmol) in 5 mL of HMPA is added 5-bromo-2-chloro-thiophene (1.00 g, 5.06 mmol) and allyl alcohol (1.03 mL, 15.2 mmol). The mixture is heated to 90° C. and stirred for 16 hours. The reaction mixture is cooled to room temperature, diluted with Et2O and washed with water. The organic layer is dried over MgSO4, filtered and concentrated in vacuo. The crude residue is purified by flash column chromatography eluting with a gradient of 10% Et2O/hexanes to 20% Et2O/hexanes to provide the product (0.18 g, 1.03 mmol) as an oil. 1H NMR (CDCl3, 300 MHz) δ9.81 (s, 1H), 6.71 (d, 1H), 6.58 (d, 1H), 3.07 (t, 2H), 2.81 (t, 2H).

後処理

  1. temperatureThe reaction mixture is cooled to room temperature
  2. washwashed with water
  3. dry with materialThe organic layer is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue is purified by flash column chromatography
  7. washeluting with a gradient of 10% Et2O/hexanes to 20% Et2O/hexanes

出典と根拠

ORDレコード
ord-3a62767deb3a4916a6a8a10d3e00875f
出典データセット
uspto-grants-2009_11
特許番号
US07612075B2

反応ノート

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