Lithium Hydroxide → HCID 60197539, compound

HRID 1472787Notes

Reaction equation

HRID 1472787 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:23]([O:25]CC)=[O:24])[S:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[CH:20]([CH3:22])[CH3:21])=[C:4]([CH:28]([CH3:30])[CH3:29])[CH:3]=1.[Li+].[OH-]>C1COCC1.CO.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:23]([OH:25])=[O:24])[S:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[CH:20]([CH3:22])[CH3:21])=[C:4]([CH:28]([CH3:30])[CH3:29])[CH:3]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 68293676HCID 68293676, compound

Product 1

HCID 60197539HCID 60197539, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4,5-bis(4-chloro-2-isopropylphenyl)thiophene-2-carboxylate (280 mg, 0.61 mmol) in THF (3 mL) and MeOH (3 mL) was added a solution of LiOH (72 mg, 3.0 mmol) in water (2 mL). The reaction was stirred at rt until complete, and then concentrated. The residue was re-dissolved in 20 mL of water and acidified with 1N aq. HCl to pH 2. The white precipitate was extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulphate and then concentrated. The residue was purified by recrystallization in a mixture solvent of ethyl acetate and hexane to afford 0.24 g (91%) of product as a white solid, 1H NMR (CDCl3, 500 MHz) δ 7.78 (s, 1H), 7.23 (d, J=2.15 Hz, 1H), 7.22 (d, J=1.88 Hz, 1H), 7.13-7.07 (m, 2H), 7.03 (dd, J1=8.23 Hz, J2=2.20 Hz, 1H), 6.89 (d, J=8.26 Hz, 1H), 2.95 (m, 2H), 1.04 (d, J—4.94 Hz, 6H), 0.98 (d, J=6.95 Hz, 6H); 13C NMR (CDCl3, 125 MHz) δ 167.13, 149.87, 149.06, 146.58, 139.45, 137.21, 135.53, 134.39, 132.79, 131.84, 131.57, 131.14, 129.01, 126.43, 126.28, 125.86, 125.77, 30.27, 30.23, 23.93.

Workup

  1. concentrationthen concentrated
  2. dissolutionThe residue was re-dissolved in 20 mL of water
  3. extractionThe white precipitate was extracted with ethyl acetate
  4. dry with materialThe organic phase was dried over anhydrous sodium sulphate
  5. concentrationconcentrated
  6. customThe residue was purified by recrystallization in a mixture solvent of ethyl acetate and hexane

Sources & evidence

ORD record
ord-47d1d3b2295e4eefb3db37d212650ef9
Source dataset
uspto-grants-2015_04
Patent number
US09012655B2

Reaction notes

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