Lithium Hydroxide → 10-(2-Fluoro-phenyl)-dec-9-enoic acid

HRID 1802980Notes

Reaction equation

HRID 1802980 reaction equation
C([O:3][C:4](=[O:21])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[F:20])C.[OH-].[Li+]>O1CCCC1>[F:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH:13]=[CH:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:4]([OH:21])=[O:3]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 6687504210-(2-Fluoro-phenyl)-dec-9-enoic acid ethyl ester

Product 1

HCID 6687513210-(2-Fluoro-phenyl)-dec-9-enoic acidYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 10-(2-fluoro-phenyl)-dec-9-enoic acid ethyl ester (420 mg, 1.44 mmol) in tetrahydrofuran (2 mL) was added 2 M aq. lithium hydroxide solution (2 mL, 4 mmol). The reaction mixture was stirred at room temperature for 16 h, then partitioned between 1 M aq. hydrochloric acid solution and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and evaporated, to afford 10-(2-fluoro-phenyl)-dec-9-enoic acid (250 mg, 66%).

Workup

  1. custompartitioned between 1 M aq. hydrochloric acid solution and ethyl acetate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-ec9fd563caf54e5a898a6d154c93ff2f
Source dataset
uspto-grants-2013_01
Patent number
US08349893B2

Reaction notes

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