Iodine → HCID 11175139、化合物

HRID 494862ノート

反応式

HRID 494862 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14](=[O:16])[CH3:15])[CH:9]=2)=[CH:4][CH:3]=1.[I-:17].[K+].II>N.O>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14](=[O:16])[CH3:15])[CH:9]=2)=[CH:6][C:7]=1[I:17]

参加物

6

反応物 3

HCID 807Iodine2 回HCID 4875Potassium Iodide2 回HCID 112181061-(4'-Hydroxy-1,1'-biphenyl-3-yl)ethanone

生成物 1

HCID 11175139HCID 11175139、化合物収率 21%

試薬・触媒・溶媒 2

HCID 222Ammonia溶媒HCID 962Water溶媒2 回

実験手順

The product from Example 136A (5.76 g, 27 mmol) was suspended in concentrated aqueous ammonia (400 mL) and treated with a solution of potassium iodide (23.3 g, 140 mmol) and iodine (7.24 g, 28.5 mmol) in water (100 mL). As the reaction did not go to completion, the mixture was treated with a second solution of potassium iodide (15.8 g, 95 mmol) and iodine (4.83 g, 19 mmol) in water (50 mL). After an hour the ammonia was removed under reduced pressure on a rotary evaporator. The mixture was extracted with EtOAc, and the combined organic phases were washed consecutively with pH 6 potassium phosphate buffer and brine, then dried (Na2SO4), concentrated, and chromatographed through silica with 1% acetic acid in a gradient of 0 to 5% EtOAc/CH2Cl2 to provide the title compound as a beige powder (21% yield). MS (ESI APCI negative ion detection) m/z 337 (M−H)−; 1HNMR (300 MHz, CDCl3) δ 2.65 (s, 3H), 5.37 (bs, 1H), 7.08 (d, 1H), 7.48-7.55 (m, 2H), 7.71 (ddd, 1H), 7.88-7.93 (m, 2H), 8.09 (dd, 1H).

後処理

  1. customAfter an hour the ammonia was removed under reduced pressure on a rotary evaporator
  2. extractionThe mixture was extracted with EtOAc
  3. washthe combined organic phases were washed consecutively with pH 6 potassium phosphate buffer and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customchromatographed through silica with 1% acetic acid in a gradient of 0 to 5% EtOAc/CH2Cl2

出典と根拠

ORDレコード
ord-bf189426b4794daea47c72bb54ffff3f
出典データセット
uspto-grants-2009_05
特許番号
US07538138B2

反応ノート

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