Lithium Hydroxide → 2'-Cyano-5-(1,2-dihydroxyethyl)-4'-methylbiphenyl-3-carboxylic acid

HRID 1845311Notes

Reaction equation

HRID 1845311 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:15]=[C:14]([CH:16]([OH:19])[CH2:17][OH:18])[CH:13]=[C:12]([C:20]([O:22]C)=[O:21])[CH:11]=1)#[N:2].[OH-].[Li+].[NH4+].[Cl-]>O1CCOCC1.O>[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:15]=[C:14]([CH:16]([OH:19])[CH2:17][OH:18])[CH:13]=[C:12]([C:20]([OH:22])=[O:21])[CH:11]=1)#[N:2]

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 25517Ammonium ChlorideHCID 58187958Methyl 2'-cyano-5-(1,2-dihydroxyethyl)-4'-methylbiphenyl-3-carboxylate

Product 1

HCID 581883262'-Cyano-5-(1,2-dihydroxyethyl)-4'-methylbiphenyl-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of methyl 2′-cyano-5-(1,2-dihydroxyethyl)-4′-methylbiphenyl-3-carboxylate (140 mg, 0.45 mmol) in 1,4-dioxane (5 mL) and water (2 mL) was added lithium hydroxide (40 mg, 1.67 mmol). The reaction mixture was stirred at rt for 6 h, and then treated with aq. NH4Cl and extracted with EtOAc (3×). The combined organic layers were dried over anhydrous MgSO4, and concentrated to afford the title compound. 1H NMR (400 MHz, acetone-d6): 8.21 (m, 1H), 8.13 (m, 1H), 7.87 (m, 1H), 7.73 (s, 1H), 7.66-7.61 (m, 1H), 7.58 (d, 1H, J=7.6 Hz), 4.91 (dd, 1H, J=7.2, 4.4 Hz), 3.75 (dd, 1H, J=11.2, 4.4 Hz), 3.65 (dd, 1H, J=11.2, 7.2 Hz), 2.47 (s, 3H).

Workup

  1. extractionextracted with EtOAc (3×)
  2. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c8eea5c8287349e9b5697514b78969b1
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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