Triphenylphosphine → HCID 21876847、化合物

HRID 1358802ノート

反応式

HRID 1358802 の反応式
N(C(OCC)=O)=NC(OCC)=O.[OH:13][C:14]1[CH:30]=[CH:29][C:17]([C:18]([C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)=[O:19])=[CH:16][CH:15]=1.O[CH:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[O:35]1[CH2:36][CH2:37][CH:32]([O:13][C:14]2[CH:30]=[CH:29][C:17]([C:18]([C:20]3[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=3)=[O:19])=[CH:16][CH:15]=2)[CH2:33][CH2:34]1

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 74956Tetrahydro-4H-pyran-4-olHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 110968174-Hydroxy-4'-nitrobenzophenone

生成物 1

HCID 21876847HCID 21876847、化合物収率 61.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Diethyl azodicarboxylate (1.47 g, 8.4 mmol) was slowly added dropwise to a solution of 4-(4-hydroxybenzoyl)-nitrobenzene (1.7 g, 7 mmol) (prepared as described in Example 1, steps), 4-hydroxytetrahydropyran (0.78 g, 7.7 mmol) and triphenylphosphine (2.2 g, 8.4 mmol) in dry tetrahydrofuran (20 mL) while stirring at room temperature under inert atmosphere. The reaction mixture was stirred for an additional hour then quenched with water (1 mL) and concentrated in vacuo. The residue was diluted with water and extracted with ethyl acetate. The combined organic extracts were washed with water and brine, dried (Na2SO4), and concentrated in vacuo. The crude product was chromatographed on silica gel (25% ethyl acetate/hexanes) and crystallized from hexanes to give 4-(4-tetrahydropyran-4-yloxybenzoyl)-nitrobenzene (1.4 g, 61%) as a white solid, m.p. 105-106° C.; Analysis for C18H17NO5: Calc.: C, 66.05; H, 5.23; N, 4.28; Found: C, 65.95; H, 5.14; N, 4.38. MS m/e (%): 283 (M+; 100).

後処理

  1. stirringThe reaction mixture was stirred for an additional hour
  2. customthen quenched with water (1 mL)
  3. concentrationconcentrated in vacuo
  4. additionThe residue was diluted with water
  5. extractionextracted with ethyl acetate
  6. washThe combined organic extracts were washed with water and brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo
  9. customThe crude product was chromatographed on silica gel (25% ethyl acetate/hexanes)
  10. customcrystallized from hexanes

出典と根拠

ORDレコード
ord-3a9bb9f1a5774ea498a5cd9d2a1aadbe
出典データセット
uspto-grants-2003_07
特許番号
US06596876B2

反応ノート

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