HCID 15234002, compound → HCID 15234003, compound

HRID 2225624Notes

Reaction equation

HRID 2225624 reaction equation
C([O:3][C:4](=[O:26])[C:5](=[O:25])[C:6]1[S:7][C:8]([O:11][CH2:12][CH2:13][O:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)=[CH:9][CH:10]=1)C>[OH-].[K+].CO>[CH:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:23]=[CH:24][C:15]=1[O:14][CH2:13][CH2:12][O:11][C:8]1[S:7][C:6]([C:5](=[O:25])[C:4]([OH:26])=[O:3])=[CH:10][CH:9]=1

Participants

4

Reactant 1

HCID 15234002HCID 15234002, compound

Product 1

HCID 15234003HCID 15234003, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

In potassium hydroxide solution (3.1 mL) was added dropwise with stirring to a chilled solution of 5-[[2-(2-naphthalenyloxy)ethyl]oxy]-alpha-oxo-2-thiopheneacetic acid ethyl ester (1.13 g) in methanol (7 mL). Almost immediately the potassium salt precipitated from the solution as a colorless solid which was filtered off and washed with methanol. The solid was partitioned between dichloromethane (100 mL) and 0.1N hydrochloric acid (35 mL) and after all solids had dissolved, the organic layer was washed with water, dried over anhydrous sodium sulfate (Na2SO4) and evaporated to yield 0.94 g of 5-[[2-(2naphthalenyloxy)ethyl]oxy]-alpha-oxo-2-thiopheneacetic acid as a yellow-orange solid. Crystallization of the acid from benzene-hexane furnished the title compound as a yellow solid, mp 152°-154 ° C.

Workup

  1. customAlmost immediately the potassium salt precipitated from the solution as a colorless solid which
  2. filtrationwas filtered off
  3. washwashed with methanol
  4. customThe solid was partitioned between dichloromethane (100 mL) and 0.1N hydrochloric acid (35 mL)
  5. dissolutionafter all solids had dissolved
  6. washthe organic layer was washed with water
  7. dry with materialdried over anhydrous sodium sulfate (Na2SO4)
  8. customevaporated

Sources & evidence

ORD record
ord-f25d424d77574dd58909feb199177ae2
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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