Lithium hydroxide, monohydrate → HCID 57508889, compound

HRID 2240797Notes

Reaction equation

HRID 2240797 reaction equation
C([O:3][C:4]([C:6]1[S:7][C:8]([S:17][CH3:18])=[C:9]2[CH2:14][C:13]([CH3:16])([CH3:15])[CH2:12][CH2:11][C:10]=12)=[O:5])C.O[Li].O>C(O)C.C1COCC1.O.OS([O-])(=O)=O.[K+]>[CH3:15][C:13]1([CH3:16])[CH2:12][CH2:11][C:10]2=[C:6]([C:4]([OH:5])=[O:3])[S:7][C:8]([S:17][CH3:18])=[C:9]2[CH2:14]1

Participants

7

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 57508888HCID 57508888, compound

Product 1

HCID 57508889HCID 57508889, compoundYield 132.3%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 516920Potassium bisulfateSolvent

Procedure

A solution of 5,5-dimethyl-3-methylsulfanyl-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylic acid ethyl ester (458 mg, 1.61 mmol) and LiOH.H2O (696 mg, 16.6 mmol) in ethanol (5 mL), THF (3 mL) and water (0.6 mL) is stirred at rt overnight. The mixture is diluted with aq. KHSO4 and extracted with DCM. The organic extract is dried over Na2SO4, filtered and the solvent is removed in vacuo to give 5,5-dimethyl-3-methylsulfanyl-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylic acid (546 mg) as a beige solid; LC-MS: tR=1.00 min, [M+1]=257.6; 1H NMR (CDCl3): δ 2.98 (t, J=7.0 Hz, 2H), 2.49 (s, 3H), 2.34 (s, 2H), 1.55 (t, J=7.0 Hz, 2H), 0.98 (s, 6H).

Workup

  1. extractionextracted with DCM
  2. extractionThe organic extract
  3. dry with materialis dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-0b59de8ac3bf4ec3af0e6e0568b8a884
Source dataset
uspto-grants-2010_05
Patent number
US07723378B2

Reaction notes

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