Triphenylphosphine → (But-3-yn-2-yloxy) Benzene

HRID 64243

반응식

HRID 64243 반응식
C([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)C(O)(C)C)(=O)C.[CH3:14][CH:15]([OH:18])[C:16]#[CH:17].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1.O>[CH3:14][CH:15]([O:18][C:4]1[CH:5]=[CH:6][CH:11]=[CH:12][CH:13]=1)[C:16]#[CH:17]

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 162393-Butyn-2-olHCID 5462977Diethyl azodicarboxylateHCID 135314191-(3-(1-Hydroxy-1-methylethyl)phenyl)ethanone

생성물 1

HCID 12519596(But-3-yn-2-yloxy) Benzene

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Phenol 27 (422.9 mg, 4.49 mmol), But-3-yn-2-ol (300 mg, 4.28 mmol) were dissolved in anhydrous THF (10 mL) under N2 atmosphere, at 0° C. was added Ph3P (1.12 g, 4.26 mmol) portion wise, stirred it for 10 min, and then DEAD (894.6 mg, 5.14 mmol) added slowly. The resultant solution was heated up to 70° C. stirred for 20 h. To the reaction mixture water added and extracted with DCM and dried organic layer on MgSO4, filtered, concentrated. Purified by flash chromatography using ethylacetate/n-hexane, 5:95) provided compound 28 (450 mg, 69%) as a solid. 1H NMR (CDCl3, 400 MHz) δ 1.67 (d, J=6.8 Hz, 3H), 2.47 (d, J=2 Hz, 1H), 4.88 (q, J=2 Hz, 1H), 6.97-7.03 (m, 3H), 7.28-7.32 (m, 2H).

후처리

  1. stirringstirred for 20 h
  2. extractionextracted with DCM and dried organic layer on MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurified by flash chromatography
  6. customprovided compound 28 (450 mg, 69%) as a solid

출처 및 근거

ORD 기록
ord-c87323b5de76448da663a06fe061e6df
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447134B2

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