Tetrahydrofuran → Methyl 6-(benzenesulphonylmethyl)-3-ethyl-2-methoxybenzoate

HRID 2177774Notes

Reaction equation

[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([O:21][CH3:22])[C:14](Br)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH2:32]1COC[CH2:33]1>O>[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([O:21][CH3:22])[C:14]([CH2:32][CH3:33])=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of methyl 6-(benzenesulphonylmethyl)-3-bromo-2-methoxybenzoate (Intermediate 65, 1.31 g) and potassium phosphate (2.02 g) in THF (9 ml) and water (4.5 ml) was degassed and palladium chloride dppf adduct with DCM (0.134 g) and triethyl borane (1M solution in THF, 4.6 ml) were added. The mixture was stirred and heated in the microwave at 140° C. for 18 minutes. The mixture was partitioned between ethyl acetate and water and the organic layer was separated, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 5-40% to give methyl 6-(benzenesulphonylmethyl)-3-ethyl-2-methoxybenzoate (0.754 g) as a colourless oil.

Workup

customwas degassed
additionpalladium chloride dppf adduct with DCM (0.134 g) and triethyl borane (1M solution in THF, 4.6 ml) were added
customThe mixture was partitioned between ethyl acetate and water
customthe organic layer was separated
dry with materialdried (Na2SO4)
filtrationfiltered
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 5-40%

Sources & evidence

ORD record: ord-6a2dd9fbd83a4434918851675b9f302d
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067905B2

Reaction notes

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