Lithium Hydroxide → HCID 44132566, compound

HRID 385460Notes

Reaction equation

HRID 385460 reaction equation
C([O:3][C:4]([C:6]1([C:11]2[CH:16]=[C:15]([O:17][CH2:18][C:19]([F:22])([F:21])[F:20])[C:14]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=3)=[C:13]([Cl:33])[CH:12]=2)[CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5])C.[Li+].[OH-]>CO.C1COCC1.O>[Cl:33][C:13]1[CH:12]=[C:11]([C:6]2([C:4]([OH:5])=[O:3])[CH2:7][CH2:8][CH2:9][CH2:10]2)[CH:16]=[C:15]([O:17][CH2:18][C:19]([F:21])([F:22])[F:20])[C:14]=1[C:23]1[CH:24]=[CH:25][C:26]([C:29]([F:30])([F:31])[F:32])=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 57995482HCID 57995482, compound

Product 1

HCID 44132566HCID 44132566, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Ethyl-1-(2-chloro-6-(2,2,2-trifluoroethoxy)-4′-(trifluoromethyl)biphenyl-4-yl)cyclopentane carboxylate (0.32 g, 0.64 mmol) was dissolved in 25 mL of MeOH/THF/H2O (10:10:5, vvl), LiOH (0.163 g, 3.88 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 1-(2-chloro-6-(2,2,2-trifluoroethoxy)-4′-(trifluoromethyl)biphenyl-4-yl)cyclopentanecarboxylic acid (0.220 g, 73%) as a white solid. 1H NMR (500 MHz, CDCl3): δ 7.69 (d, 2H), 7.41 (d, 2H), 7.26 (s, 1H), 6.92 (s, 1H), 4.22 (q, 2H), 3.71 (m, 2H), 1.98 (m, 2H), 1.81 (m, 4H).

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-0a3ed08f117c46ad9378c6916767fde6
Source dataset
uspto-grants-2013_02
Patent number
US08367863B2

Reaction notes

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