Iodine → HCID 11175139, 화합물

HRID 494862노트

반응식

HRID 494862 반응식
[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]

참가 물질

6

반응물 3

HCID 807Iodine2회HCID 4875Potassium Iodide2회HCID 112181061-(4'-Hydroxy-1,1'-biphenyl-3-yl)ethanone

생성물 1

HCID 11175139HCID 11175139, 화합물수율 21%

시약·촉매·용매 2

HCID 222Ammonia용매HCID 962Water용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-bf189426b4794daea47c72bb54ffff3f
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538138B2

반응 노트

불러오는 중…