Triphenylphosphine → Tert-butyl 4-tert-butyl-3-(cyclopropylmethoxy)phenyl carbonate

HRID 1350866Notes

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].[CH:20]1([CH2:23]O)[CH2:22][CH2:21]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>>[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][CH:20]2[CH2:22][CH2:21]2)[CH:9]=1)[O:2][C:3]([CH3:6])([CH3:5])[CH3:4]

Participants

Reactant 4

HCID 11776Triphenylphosphine

HCID 75644Cyclopropanemethanol

HCID 220568ethyl N-ethoxycarbonyliminocarbamate

HCID 15482845Tert-butyl 4-tert-butyl-3-hydroxyphenyl carbonate

Product 1

HCID 21097538Tert-butyl 4-tert-butyl-3-(cyclopropylmethoxy)phenyl carbonateYield 79.1%

Procedure

Tert-butyl 4-tert-butyl-3-hydroxyphenyl carbonate (1.5 g, 5.6 mmol), cyclopropylmethanol (0.5 mL, 6.2 mmol), triphenylphosphine (1.6 g, 6.2 mmol) and diethyl azodicarboxylate (DEAD) (1.0 mL, 6.2 mmol) were treated in the same procedure described in Example 31(a). The crude residue was applied to a silica gel chromatography column and eluted with a volume mixture of hexane and ethyl acetate (19/1 to 9/1) to furnish 1.42 g (79% yield) of the title compound as a yellow oil.

Workup

washeluted with a volume mixture of hexane and ethyl acetate (19/1 to 9/1)

Sources & evidence

ORD record: ord-de5c770a597c41a290d781575f944ef7
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07214824B2

Reaction notes

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