2-Methoxyethanol → tert-Butyl 4-tert-butyl-3-(2-methoxyethoxy)phenyl carbonate

HRID 1350861Notes

Reaction equation

[C:1](=[O:19])([O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])=[C:10]([OH:18])[CH:9]=1)[O:2][C:3]([CH3:6])([CH3:5])[CH3:4].[CH3:20][O:21][CH2:22][CH2:23]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:1](=[O:19])([O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])=[C:10]([O:18][CH2:23][CH2:22][O:21][CH3:20])[CH:9]=1)[O:2][C:3]([CH3:6])([CH3:5])[CH3:4]

Participants

Conditions

Temperature: 50 °C

Procedure

To a tetrahydrofuran (THF) (3 ml) solution of tert-butyl 4-tert-butyl-3-hydroxyphenyl carbonate (J. Org. Chem. 2001, 66, 3435) (266 mg, 1.0 mmol), 2-methoxy-ethanol (83 μL, 1.1 mmol) and triphenylphosphine (275 mg, 1.1 mmol) were added diethyl azodicarboxylate (DEAD) (165 μl, 1.1 mmol) and the mixture was stirred for 3 hours at 50° C. The solvent was removed under reduced pressure to give a residue, which was applied to a silica gel chromatography column and eluted with ethyl acetate/hexane=1/19 to furnish 0.23 g (71% yield) of the title compound as a yellow oil.

Workup

customThe solvent was removed under reduced pressure
customto give a residue, which
washeluted with ethyl acetate/hexane=1/19

Sources & evidence

ORD record: ord-e6a65eb515d645269075c7eb973fc774
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07214824B2

Reaction notes

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