Hydrochloric Acid → 2Z-ethoxy-3-{7-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-indan-4-yl}-acrylic acid

HRID 479169Notes

Reaction equation

HRID 479169 reaction equation
C([O:3][C:4](=[O:34])/[C:5](/[O:31][CH2:32][CH3:33])=[CH:6]/[C:7]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][C:19]2[N:20]=[C:21]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[O:22][C:23]=2[CH3:24])=[C:12]2[C:8]=1[CH2:9][CH2:10][CH2:11]2)C.[Li+].[OH-].Cl>O1CCOCC1.O>[CH2:32]([O:31]/[C:5](=[CH:6]\[C:7]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][C:19]2[N:20]=[C:21]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[O:22][C:23]=2[CH3:24])=[C:12]2[C:8]=1[CH2:9][CH2:10][CH2:11]2)/[C:4]([OH:34])=[O:3])[CH3:33]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 695569192Z-Ethoxy-3-{7-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-indan-4-yl}-acrylic acid ethyl ester

Product 1

HCID 180034382Z-ethoxy-3-{7-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-indan-4-yl}-acrylic acidYield 99.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

2Z-Ethoxy-3-{7-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-indan-4-yl}-acrylic acid ethyl ester (example 91 c]) (150 mg, 0.325 mmol ) was dissolved in 1.7 ml of dioxane, 0.9 ml of water were added and LiOH (0.812 ml of a 1N solution in water, 0.813 mmol) was then added slowly at room temperature. The resulting mixture was stirred overnight at room temperature. It was then poured onto ice, neutralized to pH 4 with HCl (1N) and extracted 3 times with AcOEt. The combined organic phases were washed with water, dried over magnesium sulfate and evaporated to give 140 mg (99.4%) of 2Z-ethoxy-3-{7-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-indan-4-yl}-acrylic acid as colorless crystals.

Workup

  1. additionIt was then poured onto ice
  2. extractionextracted 3 times with AcOEt
  3. washThe combined organic phases were washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-fb2230e7b4fc48879e73c7d4a19f3000
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Reaction notes

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