Sodium Hydroxide → HCID 69800656, compound

HRID 984310Notes

Reaction equation

HRID 984310 reaction equation
C([O:3][C:4](=[O:30])[C@@H:5]([O:27][CH2:28][CH3:29])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14]/[CH:15]=[CH:16]/[C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=2)=[CH:9][CH:8]=1)C.[OH-].[Na+]>C(O)C>[CH2:28]([O:27][C@@H:5]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:14]/[CH:15]=[CH:16]/[C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=2)=[CH:11][CH:12]=1)[C:4]([OH:30])=[O:3])[CH3:29]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69801593HCID 69801593, compound

Product 1

HCID 69800656HCID 69800656, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
35 °C

Procedure

(E)-(S)-2-Ethoxy-3-[4-(3-naphthalen-2-yl-allyloxy)-phenyl]-propionic acid ethyl ester (example 23) (170 mg, 0.42 mmol) was dissolved in ethanol (20 mL) at 35° C. and sodium hydroxide (1N, 2.1 mL, 2.1 mmol) added. The mixture was stirred at 35° C. for 1 h, the ethanol evaporated in vacuo and the mixture acidified to pH 1 with 1N hydrochloric acid. The product was isolated by extraction with ethyl acetate (30 mL×2). The combined organic phases were dried (MgSO4), filtered and evaporated to give 155 mg (98%) of the title compound as crystals.

Workup

  1. customthe ethanol evaporated in vacuo
  2. customThe product was isolated by extraction with ethyl acetate (30 mL×2)
  3. dry with materialThe combined organic phases were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-183ba611278b4b608ace1d6b4b8c022c
Source dataset
uspto-grants-2005_03
Patent number
US06867218B2

Reaction notes

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