Lithium Hydroxide → HCID 22708405, compound

HRID 353296Notes

Reaction equation

HRID 353296 reaction equation
[CH2:1]([C:8]1[CH:9]=[C:10]([CH2:28][CH:29]([O:35][CH2:36][CH3:37])[C:30]([O:32]CC)=[O:31])[CH:11]=[CH:12][C:13]=1[O:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][S:24]([CH3:27])(=[O:26])=[O:25])=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Li+]>C1COCC1.O>[CH2:1]([C:8]1[CH:9]=[C:10]([CH2:28][CH:29]([O:35][CH2:36][CH3:37])[C:30]([OH:32])=[O:31])[CH:11]=[CH:12][C:13]=1[O:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][S:24]([CH3:27])(=[O:26])=[O:25])=[CH:19][CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 22708421Ethyl 3-[3-benzyl-4-({4-[(methylsulfonyl)oxy]phenethyl}oxy)phenyl]-2-ethoxypropanoate

Product 1

HCID 22708405HCID 22708405, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 3-[3-benzyl-4-({4-[(methylsulfonyl)oxy]phenethyl}oxy)phenyl]-2-ethoxypropanoate—Example 5 (0.23 g; 0.42 mmole) was dissolved in THF and water (2:1), lithium hydroxide (0.014 g; 0.59 mmole) was added and the reaction mixture was stirred over night. Water was added and the THF evaporated. The remaining water was acidified with diluted hydrochloric acid and extracted with ethyl acetate. The organic phase was dried with magnesium sulfate. Evaporation gave 0.15 g (70% yield) of the product.

Workup

  1. customthe THF evaporated
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase was dried with magnesium sulfate
  4. customEvaporation

Sources & evidence

ORD record
ord-455e4bd64d3e44fb8f733ca8e782c02d
Source dataset
uspto-grants-2004_06
Patent number
US06750252B2

Reaction notes

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