Triethylamine → 3-Benzofuranacetic acid, 6-[[2',6'-dimethyl-4'-[3-(methylsulfonyl)propoxy][1,1'-biphenyl]-3-yl]methoxy]-2,3-dihydro-, (3R)-

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, in a glove box, [6-({2′,6′-dimethyl-4′-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methoxy)-1-benzofuran-3-yl]acetic acid (52 mg/mL, 0.1 mmol/mL), a solution (1:1, 0.02 mL) of methanol/THF containing triethylamine (0.007 mL/mL, 0.05 mmol/mL), a solution (1:1, 0.01 mL) of methanol/THF containing dichloro-p-cymeneruthenium (II) dimer (2.5 mg/mL, 0.004 mmol/mL) and a solution (1:1, 0.026 mL) of methanol/THF containing optically active ligand (R)-(S)JOSIPHOS (2.5 mg/mL, 0.0038 mmol/mL) were added in a glass microtube. The microtube was introduced into an autoclave and sealed, and the mixture was stirred at 50° C. for 24 hr under a hydrogen atmosphere (1 MPa). The reaction mixture was diluted with a solution (1:1, 1 mL) of normal hexane/isopropylalcohol and analyzed by high performance liquid chromatography to find the title compound (conversion ratio 27%,41% ee).

Provenance & Evidence