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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
Notes
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Reaction equation

HRID 332648 reaction equation
[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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140Toluene
Solvent

Conditions

Temperature
45 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-7673d73a4ea74ad1aee0573a2b85b885
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08877774B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes