Epibromohydrin → Tert-butyldimethyl(4-(oxiran-2-ylmethoxy)phenoxy)silane

HRID 221634

Reaction equation

[C:1]([Si:5]([CH3:15])([CH3:14])[O:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:16]([CH:18]1[O:20][CH2:19]1)Br>>[C:1]([Si:5]([CH3:15])([CH3:14])[O:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:16][CH:18]2[CH2:19][O:20]2)=[CH:11][CH:12]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 18430Epibromohydrin

HCID 5973884-(tert-Butyldimethylsiloxy)phenol

Product 1

HCID 19385012Tert-butyldimethyl(4-(oxiran-2-ylmethoxy)phenoxy)silaneYield 21%

Procedure

Synthesis followed SP3a, using 4.1 mmol 4-(tert-Butyl-dimethyl-silanyloxy)-phenol and racemic epibromohydrine to give the title compound upon purification by Flash Master Personal (20 g silica gel cartridge, PE to PE/ethyl acetate 15:1) with 21% yield.

Workup

customSynthesis

Sources & evidence

ORD record: ord-95e5a9dc1d794b0b99703425051ff954
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207174B2

Linked notes

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