6-(t-Butyldimethylsilyloxy)-1-hexyne → 5-[6-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-1-hexynyl]-2H-1-benzopyran-2-one

HRID 328013Notes

Reaction equation

HRID 328013 reaction equation
[O:1]=[C:2]1[CH:7]=[CH:6][C:5]2[C:8](OS(C(F)(F)F)(=O)=O)=[CH:9][CH:10]=[CH:11][C:4]=2[O:3]1.[CH3:20][C:21]([Si:24]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]#[CH:33])([CH3:26])[CH3:25])([CH3:23])[CH3:22]>>[CH3:23][C:21]([Si:24]([CH3:25])([CH3:26])[O:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]#[C:33][C:8]1[C:5]2[CH:6]=[CH:7][C:2](=[O:1])[O:3][C:4]=2[CH:11]=[CH:10][CH:9]=1)([CH3:20])[CH3:22]

Participants

3

Reactant 2

HCID 110094486-(t-Butyldimethylsilyloxy)-1-hexyneHCID 54079840trifluoromethanesulfonic acid 2-oxo-2H-1-benzopyran-5-yl ester

Product 1

HCID 199219065-[6-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-1-hexynyl]-2H-1-benzopyran-2-oneYield 87%

Procedure

Using the procedure of example 120, trifluoromethanesulfonic acid 2-oxo-2H-1-benzopyran-5-yl ester from example 119 was converted to the title compound by reaction with (1,1-dimethylethyl)(5-hexynyloxy)dimethylsilane. The product was a solid, obtained in 87% yield.

Sources & evidence

ORD record
ord-6261b3fa888a4b2187de315653995fa0
Source dataset
uspto-grants-1993_12
Patent number
US05273999

Reaction notes

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