Lithium Hydroxide → 3-Benzyloxy-5-isopropyl-thiophene-2-carboxylic acid

HRID 1445332Notes

Reaction equation

HRID 1445332 reaction equation
[CH2:1]([O:8][C:9]1[CH:13]=[C:12]([CH:14]([CH3:16])[CH3:15])[S:11][C:10]=1[C:17]([O:19]C)=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Li+]>O1CCCC1.CO.O>[CH2:1]([O:8][C:9]1[CH:13]=[C:12]([CH:14]([CH3:16])[CH3:15])[S:11][C:10]=1[C:17]([OH:19])=[O:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 21961236Methyl 3-benzyloxy-5-isopropyl-thiophene-2-carboxylate

Product 1

HCID 219612383-Benzyloxy-5-isopropyl-thiophene-2-carboxylic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
22 °C

Procedure

1.16 g of methyl 3-benzyloxy-5-isopropyl-thiophene-2-carboxylate were dissolved in 10 ml of tetrahydrofuran (THF) and 10 ml of methanol, and a solution of 1.7 g of lithium hydroxide in 10 ml of water was added. The reaction mixture was stirred at 22° C. for 72 h. Methanol and THF were stripped off in the rotary evaporator. While cooling in ice, the reaction mixture was adjusted to pH=4 with 2 molar hydrochloric acid and extracted twice with 50 ml of ethyl acetate each time. The combined organic phases were dried over sodium sulfate and concentrated.

Workup

  1. customMethanol and THF were stripped off in the rotary evaporator
  2. temperatureWhile cooling in ice
  3. extractionextracted twice with 50 ml of ethyl acetate each time
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-969aa52c14c049f7bfb67d773daa699d
Source dataset
uspto-grants-2010_02
Patent number
US07666848B2

Reaction notes

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