Hydrochloric Acid → HCID 57581229, compound

HRID 548551Notes

Reaction equation

HRID 548551 reaction equation
C[O:2][C:3](=[O:31])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]#[C:15][C:16]2[CH:21]=[C:20]([C:22]#[C:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:19]=[C:18]([Br:30])[CH:17]=2)=[CH:8][CH:7]=1.[Li+].[OH-].O.Cl>C1COCC1.CO>[Br:30][C:18]1[CH:17]=[C:16]([C:15]#[C:14][CH2:13][O:12][C:9]2[CH:8]=[CH:7][C:6]([O:5][CH2:4][C:3]([OH:31])=[O:2])=[CH:11][CH:10]=2)[CH:21]=[C:20]([C:22]#[C:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:19]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 67157886HCID 67157886, compound

Product 1

HCID 57581229HCID 57581229, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of {4-[3-(3-bromo-5-phenylethynyl-phenyl)-prop-2-ynyloxy]-phenoxy}-acetic acid methyl ester (66 mg, 0.14 mmol) in THF (1.5 ml) and methanol (0.3 ml) was added a ice-cold solution of LiOH (1 M, 2 ml). The reaction mixture was stirred at 0° C. for 45 min., after which water (10 ml) and aqueous HCl (1M, 2 ml) were added. The mixture was extracted with ethyl acetate (2×5 ml), and the combined organic phases were dried and evaporated to give the title compound in 64 mg (100%) yield.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (2×5 ml)
  2. customthe combined organic phases were dried
  3. customevaporated

Sources & evidence

ORD record
ord-d2549e01778449eca7d1b490aaef95fb
Source dataset
uspto-grants-2011_05
Patent number
US07943612B2

Reaction notes

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