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

HRID 1848802Notes

Reaction equation

HRID 1848802 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:5]=[C:4]([CH3:16])[C:3]=1[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][O:24][C:25]2[CH:37]=[CH:36][C:28]3[C:29]([CH2:32][C:33]([OH:35])=[O:34])=[CH:30][O:31][C:27]=3[CH:26]=2)[CH:18]=1.CO.C1COCC1.C(N(CC)CC)C>CCCCCC.C(O)(C)C.C[C@@H](P(C1CCCCC1)C1CCCCC1)[C]1[C](P(C2C=CC=CC=2)C2C=CC=CC=2)[CH][CH][CH]1.[CH]1[CH][CH][CH][CH]1.[Fe]>[CH3:16][C:4]1[CH:5]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:7]=[C:2]([CH3:1])[C:3]=1[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][O:24][C:25]2[CH:37]=[CH:36][C:28]3[C@@H:29]([CH2:32][C:33]([OH:35])=[O:34])[CH2:30][O:31][C:27]=3[CH:26]=2)[CH:18]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 21899815MeOH tetrahydrofuran3×HCID 86706791[6-({2',6'-Dimethyl-4'-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methoxy)-1-benzofuran-3-yl]acetic acid

Product 1

HCID 714572853-Benzofuranacetic acid, 6-[[2',6'-dimethyl-4'-[3-(methylsulfonyl)propoxy][1,1'-biphenyl]-3-yl]methoxy]-2,3-dihydro-, (3R)-Yield 27%

Reagents, catalysts & solvents 2

HCID 178461697HCID 178461697, compoundCatalystHCID 21585144Isopropanol hexaneSolvent

Conditions

Temperature
50 °C

Procedure

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).

Workup

  1. additionThe microtube was introduced into an autoclave
  2. customsealed

Sources & evidence

ORD record
ord-ba81b552ff6a4922aeb0edc29bb882ba
Source dataset
uspto-grants-2015_02
Patent number
US08952185B2

Reaction notes

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