Trimethylsilylacetylene → HCID 68286487, compound

HRID 1754033Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1)[CH2:6]Br.[C:13]([Si:15]([CH3:18])([CH3:17])[CH3:16])#[CH:14]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:6][C:14]#[C:13][Si:15]([CH3:18])([CH3:17])[CH3:16])[CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1

Participants

Reactant 2

HCID 66111Trimethylsilylacetylene

HCID 12744903,5-Dimethoxybenzyl Bromide

Product 1

HCID 68286487HCID 68286487, compound

Procedure

In any or all of the above embodiments, converting the 3,5-methoxybenzoic acid to the (E)-5-(2-halo-3-iodoallyl)-1,3-phenylene bis(2,2-dimethylpropanoate) may include (1) reducing the 3,5-methoxybenzoic acid to produce 3,5-dimethoxybenzyl alcohol, (2) brominating the 3,5-dimethoxybenzyl alcohol to produce 3,5-dimethoxybenzyl bromide, (3) reacting the 3,5-dimethoxybenzyl bromide with ethynyl trimethylsilane to produce (3-(3,5-dimethoxyphenyl)prop-1-ynyl)trimethylsilane, (4) desilylating the (3-(3,5-dimethoxyphenyl)prop-1-ynyl)trimethylsilane to produce 1,3-dimethoxy-5-(prop-2-ynyl)benzene, (5) adding protecting groups to the 1,3-dimethoxy-5-(prop-2-ynyl)benzene to produce 5-(prop-2-ynyl)-1,3-phenylene bis(2,2-dimethylpropanoate), wherein the protecting groups are pivaloyl groups added by reacting the 1,3-dimethoxy-5-(prop-2-ynyl)benzene with boron tribromide and then with pivaloyl chloride, and (6) halogenating the 5-(prop-2-ynyl)-1,3-phenylene bis(2,2-dimethylpropanoate) to produce (E)-5-(2-halo-3-iodoallyl)-1,3-phenylene bis(2,2-dimethylpropanoate), wherein the 2-halo corresponds to R4.

Sources & evidence

ORD record: ord-ff71c8a5604648109a052bc9b76031cc
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09169182B2

Reaction notes

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