Water → HCID 68979664, compound

HRID 749481Notes

Reaction equation

HRID 749481 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:12]([O:14]C)=[O:13])[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1.[Li+].[OH-].O>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C:12]([OH:14])=[O:13])[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 68978267HCID 68978267, compound

Product 1

HCID 68979664HCID 68979664, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 3-fluoro-5,6,7,8-tetrahydronaphthalene-1-carboxylate (37 mg, 0.18 mmol), LiOH (27 mg, 1.1 mmol), water (2 mL) and THF (1 mL) was stirred at room temperature overnight and then partitioned between ether and water. The aqueous layer was extracted thrice with ether and then repeatedly with ethyl acetate. The combined organic solutions were dried over MgSO4 and the solvent was removed by evaporation. There was obtained 15 mg (43%) of 3-fluoro-5,6,7,8-tetrahydronaphthalene-1-carboxylic acid as a white solid. 1H NMR (500 MHz, CD3CO CD3): 1.8 (m, 4H), 2.8 (m, 2H), 3.1 (m, 2H), 7.0 (m, 1H), 7.6 (m, 1H).

Workup

  1. custompartitioned between ether and water
  2. extractionThe aqueous layer was extracted thrice with ether
  3. dry with materialThe combined organic solutions were dried over MgSO4
  4. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-8a772175fd864936b75cec8023ac872b
Source dataset
uspto-grants-2008_07
Patent number
US07402581B2

Reaction notes

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