Ethyl Acetate → HCID 21949634, compound

HRID 2215203Notes

Reaction equation

HRID 2215203 reaction equation
C([O:3][C:4](=[O:31])[CH:5]([O:28][CH2:29][CH3:30])[CH2:6][C:7]1[C:12]2[S:13][CH:14]=[CH:15][C:11]=2[C:10]([O:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]([CH3:27])([CH3:26])[CH3:25])[O:21][C:22]=2[CH3:23])=[CH:9][CH:8]=1)C.[OH-].[Na+].CCOC(C)=O>C1COCC1.CCO>[C:24]([C:20]1[O:21][C:22]([CH3:23])=[C:18]([CH2:17][O:16][C:10]2[C:11]3[CH:15]=[CH:14][S:13][C:12]=3[C:7]([CH2:6][CH:5]([O:28][CH2:29][CH3:30])[C:4]([OH:31])=[O:3])=[CH:8][CH:9]=2)[N:19]=1)([CH3:27])([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 69487539HCID 69487539, compound

Product 1

HCID 21949634HCID 21949634, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

0.125 g of the above prepared 3-[4-(2-tert-butyl-5-methyl-oxazol-4-ylmethoxy)-benzo[b]thiophen-7-yl]-2-ethoxy-propionic acid ethyl ester (0.281 mmol) was dissolved in 1.7 ml of THF/EtOH=1/1, treated with 0.840 ml of 1N NaOH (3 eq.), and kept at ambient temperature for 1.0 h. The reaction mixture was then poured onto crashed ice/AcOEt/HCl dil., the aqueous phase reextracted once more with AcOEt, the combined organic layers washed with water, dried over magnesium sulfate, and evaporated to dryness. Crystallization from hexane/AcOEt yielded finally 0.111 g of the title compound as white crystals of mp. 179–80°.

Workup

  1. additionThe reaction mixture was then poured
  2. washthe combined organic layers washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated to dryness
  5. customCrystallization from hexane/AcOEt

Sources & evidence

ORD record
ord-836181999437444599c869d6994e4596
Source dataset
uspto-grants-2006_09
Patent number
US07109225B2

Reaction notes

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