Trimethylsilylacetylene → Methyl 2-hydroxy-4-trimethylsilylethynylbenzoate

HRID 861765Notes

Reaction equation

[OH:1][C:2]1[CH:11]=[C:10](I)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH3:13][Si:14]([C:17]#[CH:18])([CH3:16])[CH3:15]>>[OH:1][C:2]1[CH:11]=[C:10]([C:18]#[C:17][Si:14]([CH3:16])([CH3:15])[CH3:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

Reactant 2

HCID 66111Trimethylsilylacetylene

HCID 11380407Methyl 4-iodosalicylate

Product 1

HCID 22641103Methyl 2-hydroxy-4-trimethylsilylethynylbenzoateYield 85.5%

Procedure

Following the basic procedure of Example 1(a), by reacting 34 g (122 mmol) of methyl 2-hydroxy-4-iodobenzoate with 34 ml (244 mmol) of trimethylsilylacetylene, 25.9 g (85%) of the expected compound were obtained in the form of a brown oil.

Sources & evidence

ORD record: ord-84e2fcdd17854d3caa3b0165329d7ede
Source dataset: uspto-grants-1998_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05716624

Reaction notes

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