Lithium hydroxide, monohydrate → HCID 15228843, compound

HRID 257644Notes

Reaction equation

HRID 257644 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([S:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28]C)=[O:27])[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[OH-].[Li+]>CO.O>[C:1]1([C:7]2[N:8]=[C:9]([S:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 15228842HCID 15228842, compound

Product 1

HCID 15228843HCID 15228843, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl 8-[(4,5-diphenyl-2-oxazolyl)thio]octanoate (2.0 g, 4.9 mol) was dissolved in methanol (30 mL). A solution of lithium hydroxide monohydrate (0.41 g, 9.8 mmol) in water (8 mL) was added and the mixture heated to reflux for 1 hour. After cooling to room temperature, the methanol was removed in vacuo, the residue diluted with water and acidified to about pH 2 using dilute hydrochloric acid solution. The mixture was extracted with EtOAc, the combined extracts dried over MgSO4 and concentrated. The residue was chromatographed on a column of silica gel using CH2Cl2 /MeOH (95/5) as eluent to give 8-[(4,5-diphenyl-2-oxazolyl)thio]octanoic acid (1.70 g, 88%).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 1 hour
  3. customthe methanol was removed in vacuo
  4. additionthe residue diluted with water
  5. extractionThe mixture was extracted with EtOAc
  6. dry with materialthe combined extracts dried over MgSO4
  7. concentrationconcentrated
  8. customThe residue was chromatographed on a column of silica gel

Sources & evidence

ORD record
ord-f8d817d1c1c245a69778abb928a2b169
Source dataset
uspto-grants-1993_11
Patent number
US05262540

Reaction notes

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