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

HRID 64243

反応式

HRID 64243 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c87323b5de76448da663a06fe061e6df
出典データセット
uspto-grants-2016_09
特許番号
US09447134B2

関連ノート

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