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

HRID 332648Notes

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]

Participants

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

waitat RT for 16 hours
concentrationThe reaction mixture was concentrated under reduced pressure
customThe crude material was purified by silica gel chromatography
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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