Triphenylphosphine → HCID 21876847, 화합물

HRID 993367노트

반응식

HRID 993367 반응식
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

참가 물질

6

반응물 4

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

생성물 1

HCID 21876847HCID 21876847, 화합물수율 61.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Diethyl azodicarboxylate (1.47 g, 8.4 mmol) was slowly added dropwise to a solution of 4-(4-hydroxybenzoyl)-nitrobenzene (1.7 g, 7mmol) (prepared as described in Example 1, steps), 4-hydroxytetrahydropyran (0,78 g, 7.7 mmol) and triphenylphosphine (2.2 g, 8.4mmol) 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, 3.14; N, 4.38. MS m/e (%): 283 (M+; 100).

후처리

  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 The combined organic extracts
  6. washwere 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

출처 및 근거

ORD 기록
ord-70b3195a97b8420b9efb0b8085677d64
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06472536B1

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