Tert-butyl 2-((1-(4-fluorophenyl)cyclohexyl)methoxy)acetate → 2-((1-(4-Fluorophenyl)cyclohexyl)methoxy)acetic acid

HRID 71266Notes

Reaction equation

HRID 71266 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:14][O:15][CH2:16][C:17]([O:19]C(C)(C)C)=[O:18])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1>FC(F)(F)C(O)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH2:14][O:15][CH2:16][C:17]([OH:19])=[O:18])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 66685225Tert-butyl 2-((1-(4-fluorophenyl)cyclohexyl)methoxy)acetate

Product 1

HCID 666856282-((1-(4-Fluorophenyl)cyclohexyl)methoxy)acetic acidYield 96%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl 2-((1-(4-fluorophenyl)cyclohexyl)methoxy)acetate (100 mg, 310 μmol) in trifluoroacetic acid (1 mL) was stirred at room temperature for 85 min. TFA was removed under reduced pressure, followed by co-evaporation with ether to obtain the crude 2-((1-(4-fluorophenyl)cyclohexyl)methoxy)acetic acid (79 mg, 96% yield) as a white solid. 1H NMR (400 MHz, CDCl3): δ ppm 7.30-7.43 (m, 2H), 6.93-7.17 (m, 2H), 3.91 (s, 2H), 3.46 (s, 2H), 2.13 (d, 2H), 1.60-1.76 (m, 2H), 1.55 (dd, 3H), 1.26-1.44 (m, 3H).

Workup

  1. customTFA was removed under reduced pressure

Sources & evidence

ORD record
ord-55695e43f93246208f6e63ee243e751f
Source dataset
uspto-grants-2014_09
Patent number
US08822510B2

Reaction notes

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