Sulfuric Acid → 5-(4-Hydroxytetrahydrofuran-3-yloxy)-4'-methylbiphenyl-3-carboxylic acid

HRID 1845326Notes

Reaction equation

HRID 1845326 reaction equation
[OH:1][CH:2]1[CH2:6][O:5][CH2:4][CH:3]1[O:7][C:8]1[CH:9]=[C:10]([C:21]([O:23]C)=[O:22])[CH:11]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[CH:13]=1.[OH-].[Li+].OS(O)(=O)=O>O1CCOCC1.O>[OH:1][CH:2]1[CH2:6][O:5][CH2:4][CH:3]1[O:7][C:8]1[CH:9]=[C:10]([C:21]([OH:23])=[O:22])[CH:11]=[C:12]([C:14]2[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=2)[CH:13]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 3939Lithium HydroxideHCID 58188331Methyl 5-(4-hydroxytetrahydrofuran-3-yloxy)-4'-methylbiphenyl-3-carboxylate

Product 1

HCID 581882075-(4-Hydroxytetrahydrofuran-3-yloxy)-4'-methylbiphenyl-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of methyl 5-(4-hydroxytetrahydrofuran-3-yloxy)-4′-methylbiphenyl-3-carboxylate (140 mg, 0.40 mmol) in 1,4-dioxane (2.8 mL) and water (2.8 mL) was added lithium hydroxide (50 mg, 2.1 mmol). The reaction mixture was stirred at room temperature for 2 hours, and then acidifized with 2N aq. H2SO4 to pH 4-5 and concentrated in vacuo. The residue was treated with water and extracted with EtOAc (10 mL×2). The combined organic layers were dried (MgSO4) and concentrated to afford the title compound. 1H NMR (CD3OD, 400 MHz): 7.87 (t, J=1.6 Hz, 1H), 7.55-7.51 (m, 3H), 7.42 (t, J=2.0 Hz, 1H), 7.28 (d, J=7.6 Hz, 2H), 4.84 (d, J=4.4 Hz, 1H), 4.38 (d, J=4.0 Hz, 1H), 4.23 (dd, J=10.4, 4.4 Hz, 1H), 4.05 (dd, J=9.6, 4.4 Hz, 1H), 3.94 (dd, J=10.4, 1.6 Hz, 1H), 3.77 (dd, J=9.6, 1.6 Hz, 1H), 2.38 (s, 3H).

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was treated with water
  3. extractionextracted with EtOAc (10 mL×2)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-740546b37a0946879f1b39bcdd266e21
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

Loading…