Lithium Hydroxide → HCID 44132561, compound

HRID 385463Notes

Reaction equation

HRID 385463 reaction equation
C([O:3][C:4](=[O:33])[CH:5]([C:10]1[CH:15]=[C:14]([O:16][CH2:17][C:18]([F:21])([F:20])[F:19])[C:13]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)=[C:12]([Cl:32])[CH:11]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])C.[Li+].[OH-]>CO.C1COCC1.O>[Cl:32][C:12]1[CH:11]=[C:10]([CH:5]([CH2:6][CH:7]([CH3:9])[CH3:8])[C:4]([OH:33])=[O:3])[CH:15]=[C:14]([O:16][CH2:17][C:18]([F:20])([F:21])[F:19])[C:13]=1[C:22]1[CH:23]=[CH:24][C:25]([C:28]([F:29])([F:30])[F:31])=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 57995579HCID 57995579, compound

Product 1

HCID 44132561HCID 44132561, compoundYield 24.7%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Ethyl-2-(2-chloro-6-(2,2,2-trifluoroethoxy)-4′-(trifluoromethyl)biphenyl-4-yl)-4-methylpentanoate (0.35 g, 0.733 mmol) was dissolved in 25 mL of MeOH/THF/H2O (10:10:5, vvl), LiOH (0.176 g, 7.33 mmol) was added. The reaction mixture was stirred for 5 h at room temperature and concentrated under reduced pressure. Water (10 mL) was added and the reaction mixture was extracted with EtOAc (3×10 mL). The combined organic phases were dried over Na2SO4, filtered and evaporated under reduced pressure. Purification by column chromatography over silica gel (DCM/MeOH, 95:5) gave the compound 2-(2-chloro-6-(2,2,2-trifluoroethoxy)-4′-(trifluoromethyl)biphenyl-4-yl)-4-methylpentanoic acid (0.085 g) as a white solid. 1H NMR (500 MHz, CDCl3): δ 7.69 (d, 2H), 7.41 (d, 2H), 7.20 (s, 1H), 6.86 (s, 1H), 4.23 (q, 2H), 3.71 (t, 1H), 2.01 (m, 1H), 1.73 (m, 1H), 1.58 (m, 1H), 0.98 (d, 6H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionWater (10 mL) was added
  3. extractionthe reaction mixture was extracted with EtOAc (3×10 mL)
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customPurification by column chromatography over silica gel (DCM/MeOH, 95:5)

Sources & evidence

ORD record
ord-eb38a5036394403bb610b49148cf6baa
Source dataset
uspto-grants-2013_02
Patent number
US08367863B2

Reaction notes

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