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

HRID 1022117
Notes
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Reaction equation

HRID 1022117 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 3776IsopropanolSolvent
HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
65 °C

Procedure

To the solution of 282c (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). 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 282d (12.0 g, 86%) as 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-10056bc60556480da869edef4c8dfeb8
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08716274B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes