Lithium Hydroxide → HCID 9822433, compound

HRID 1250105Notes

Reaction equation

HRID 1250105 reaction equation
[OH-].[Li+].C([O:7][C:8](=[O:36])[CH2:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13](/[CH:17]=[CH:18]/[CH2:19][O:20][C:21](=[O:35])[N:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:12]=1)(C)(C)C>CO.O1CCCC1>[C:29]1([N:22]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:21]([O:20][CH2:19]/[CH:18]=[CH:17]/[C:13]2[CH:12]=[C:11]([CH:16]=[CH:15][CH:14]=2)[O:10][CH2:9][C:8]([OH:36])=[O:7])=[O:35])[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86757708HCID 86757708, compound

Product 1

HCID 9822433HCID 9822433, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.0M Lithium hydroxide (1.46 mL, 1.46 mmol) was added to a solution of trans-[3-(3-diphenylcarbamoyloxypropenyl)phenoxy}acetic acid tert-butyl ester (0.56 g, 1.22 mmol) in methanol (2 mL), tetrahydrofuran (2 mL) at room temperature under a nitrogen atmosphere. The mixture was stirred at room temperature for 3 hours. The solvent was evaporated, water was added followed by 2N hydrochloric acid to pH 1-2, and the product was extracted with ethyl acetate. The extract was washed with water, brine, dried over magnesium sulfate, and concentrated to dryness. Recrystallization in diethyl ether gave trans-[3-(3-diphenylcarbamoyloxypropenyl)phenoxy}acetic acid as a white crystalline solid (0.38 g, 78%), m.p. 112.4-113.7° C.

Workup

  1. customThe solvent was evaporated
  2. additionwater was added
  3. extractionthe product was extracted with ethyl acetate
  4. washThe extract was washed with water, brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated to dryness
  7. customRecrystallization in diethyl ether

Sources & evidence

ORD record
ord-10e103d784a4492984eb0769b159f3d6
Source dataset
uspto-grants-2002_01
Patent number
US06335459B1

Reaction notes

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