Lithium hydroxide, monohydrate → 2-(2-Thiazolinylthio)-hydrocinnamic acid

HRID 478042Notes

Reaction equation

HRID 478042 reaction equation
C([O:3][C:4](=[O:19])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[S:13][C:14]1[S:15][CH2:16][CH2:17][N:18]=1)C.O.[OH-].[Li+]>C1COCC1.O>[S:15]1[CH2:16][CH2:17][N:18]=[C:14]1[S:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[CH2:6][CH2:5][C:4]([OH:19])=[O:3]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 572061812-(2-Thiazolinylthio)hydrocinnamic acid ethyl ester

Product 1

HCID 570633422-(2-Thiazolinylthio)-hydrocinnamic acid

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A mixture of 250 mg of 2-(2-thiazolinylthio)hydrocinnamic acid ethyl ester, 36 mg of lithium hydroxide monohydrate and 5 ml of THF/water 9:1 is stirred at room temperature for 5 days and then concentrated to dryness by evaporation. The residue is taken up in water, washed with ethyl acetate, adjusted to pH 5 with 0.5N HCl and extracted with ethyl acetate. The extracts are washed with water, dried with sodium sulphate, concentrated by evaporation and chromatographed on silica gel with eluant R. Rf (R)=0.22.

Workup

  1. concentrationconcentrated to dryness by evaporation
  2. washwashed with ethyl acetate
  3. extractionextracted with ethyl acetate
  4. washThe extracts are washed with water
  5. dry with materialdried with sodium sulphate
  6. concentrationconcentrated by evaporation
  7. customchromatographed on silica gel with eluant R

Sources & evidence

ORD record
ord-3f39a6c491db44bc861b222258d43e47
Source dataset
uspto-grants-1989_12
Patent number
US04889869

Reaction notes

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