Water → 5,5-dimethyl-4H,5H,6H-cyclopenta[b]thiophene-2-carboxylic acid

HRID 1843277Notes

Reaction equation

HRID 1843277 reaction equation
[CH3:1][C:2]1([CH3:15])[CH2:14][C:5]2[S:6][C:7]([C:9]([O:11]CC)=[O:10])=[CH:8][C:4]=2[CH2:3]1.O.[OH-].[Li+]>CC(O)C.O1CCCC1>[CH3:1][C:2]1([CH3:15])[CH2:14][C:5]2[S:6][C:7]([C:9]([OH:11])=[O:10])=[CH:8][C:4]=2[CH2:3]1

Participants

6

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 58043720Ethyl 5,5-Dimethyl-5,6-dihydro-4H-cyclopenta[b]thiophene-2-carboxylate

Product 1

HCID 580439285,5-dimethyl-4H,5H,6H-cyclopenta[b]thiophene-2-carboxylic acidYield 86.1%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 131c (16.0 g, 71.0 mmol) in propan-2-ol (200 mL), tetrahydrofuran (200 mL), and water (200 mL) was added lithium hydroxide (6.82 g, 284 mmol). See FIG. 15. The reaction mixture was heated at 65° C. for 5 h. The organic solvents were removed under reduced pressure. The pH of the residue was adjusted to 1.0 with hydrochloride acid (12M). The precipitate was collected by filtration and dried in vacuo to afford 131d (12.0 g, 86%) as a white solid. MS-ESI: [M+H]+ 196.9

Workup

  1. customThe organic solvents were removed under reduced pressure
  2. filtrationThe precipitate was collected by filtration
  3. customdried in vacuo

Sources & evidence

ORD record
ord-dbb77868d75346edafd981ebe11d9962
Source dataset
uspto-grants-2015_02
Patent number
US08946213B2

Reaction notes

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