(Z)-3-(Tributylstannyl)prop-2-en-1-ol → Methyl 3-bromo-6-((2-(3-hydroxyprop-1-enyl)benzenesulfonyl)methyl)-2-methoxybenzoate

HRID 2177732Notes

Reaction equation

[Br:1][C:2]1[C:3]([O:23][CH3:24])=[C:4]([C:9]([CH2:12][S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2Br)(=[O:15])=[O:14])=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C([Sn](CCCC)(CCCC)/[CH:30]=[CH:31]\[CH2:32][OH:33])CCC>C1(C)C=CC=CC=1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[Br:1][C:2]1[C:3]([O:23][CH3:24])=[C:4]([C:9]([CH2:12][S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH:30]=[CH:31][CH2:32][OH:33])(=[O:15])=[O:14])=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

Conditions

Temperature: 30 °C

Procedure

Bis-(tri-tert-butylphosphine)palladium (0.031 g) was added to a degassed solution of methyl 3-bromo-6-(2-bromobenzenesulphonylmethyl)-2-methoxybenzoate (Intermediate 66, 0.286 g) and 3-tributylstannyl-(Z)-prop-2-en-1-ol (prepared according to Webb et al, Tetrahedron, 2008, 64, 4778, 0.27 ml) in toluene (3 ml) and the resultant mixture was stirred at room temperature for 3 hours then heated at 30° C. for 2 hours. After cooling, the mixture was filtered through Celite and the filtrate was evaporated to dryness. The residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-60% to give methyl 3-bromo-6-((2-(3-hydroxyprop-1-enyl)benzenesulfonyl)methyl)-2-methoxybenzoate as a mixture of E and Z isomers.

Workup

temperatureAfter cooling
filtrationthe mixture was filtered through Celite
customthe filtrate was evaporated to dryness
customThe residue was purified by chromatography on silica
washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-60%

Sources & evidence

ORD record: ord-07f8da335965484ba1e5fbadf6bc0bcb
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067905B2

Reaction notes

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