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1,8-Diazabicyclo(5.4.0)undec-7-ene → 2-(8-(3-(Azido(phenyl)methyl)phenoxy)octyl)-1,3-dioxolane

HRID 332648
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HRID 332648 반응식
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:16]=[C:17]([CH:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)O)[CH:18]=[CH:19][CH:20]=1.C1(P([N:43]=[N+:44]=[N-:45])(C2C=CC=CC=2)=O)C=CC=CC=1.C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1>[N:43]([CH:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][CH:18]=1)[O:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH:2]1[O:3][CH2:4][CH2:5][O:1]1)=[N+:44]=[N-:45]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 71093342(3-(8-(1,3-Dioxolan-2-yl)octyloxy)phenyl)(phenyl)methanol

생성물 1

HCID 710931432-(8-(3-(Azido(phenyl)methyl)phenoxy)octyl)-1,3-dioxolane수율 64%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
45 °C

실험 절차

To a stirred solution of (3-(8-(1,3-dioxolan-2-yl)octyloxy)phenyl)-(phenyl)methanol (1.63 g, 4.24 mmol) in toluene (10 mL) under an atmosphere of nitrogen, diphenylphosphoryl azide (1.10 mL, 5.10 mmol) and DBU (0.77 mL, 5.11 mmol) was added. The reaction mixture was stirred at 45° C. for 3 hours and then at RT for 16 hours. The reaction mixture was concentrated under reduced pressure. The crude material was purified by silica gel chromatography eluting with 0-100% ethyl acetate in iso-hexane to afford impure title compound (1.11 g, 64%). This material was used directly in the next step.

후처리

  1. waitat RT for 16 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customThe crude material was purified by silica gel chromatography
  4. washeluting with 0-100% ethyl acetate in iso-hexane

출처 및 근거

ORD 기록
ord-7673d73a4ea74ad1aee0573a2b85b885
출처 데이터셋
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08877774B2

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