Iodine → HCID 10877236, 화합물

HRID 1008760노트

반응식

HRID 1008760 반응식
[C:1]1([CH2:7][C:8]#[C:9][CH2:10][OH:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.II>C(Cl)Cl.O=[Mn]=O>[C:1]1([CH2:7][C:8]#[C:9][CH:10]=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

5

반응물 2

HCID 807IodineHCID 12474205HCID 12474205, 화합물

생성물 1

HCID 10877236HCID 10877236, 화합물

시약·촉매·용매 2

HCID 14801Manganese dioxide촉매2회HCID 6344Dichloromethane용매

실험 절차

4-Phenyl-2-butyn-1-ol (550 mg; 3.76 mmol, obtained as described in Bull. Soc. Chim. Fr, 1954, 816) was dissolved in DCM (10 mL) and MnO2 (1.64 g; 18.8 mmol) was added. The mixture was stirred at rt and the reaction was monitored by TLC (EtOAc/c-Hex 10/90, staining with iodine). MnO2 was regularly added (1.64 g; 18.8 mmol; three times). MnO2 was removed by filtration on a bed of celite. After washing the celite with DCM, the filtrates were then concentrated under reduced pressure. Purification of the crude by flash chromatography on silica (gradient EtOAc/c-Hex 5:95 to 30:70) gave the title compound as an range oil (60 mg, 11% yield). 1H NMR (CDCl3) δ: 9.22 (s, 1H), 7.26 (m, 5H), 3.80 (s, 2H).

후처리

  1. customMnO2 was removed by filtration on a bed of celite
  2. washAfter washing the celite with DCM
  3. concentrationthe filtrates were then concentrated under reduced pressure
  4. customPurification of the crude by flash chromatography on silica (gradient EtOAc/c-Hex 5:95 to 30:70)

출처 및 근거

ORD 기록
ord-3a6e635dbad84a72bf98816adb22c0d6
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07973039B2

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