Trifluoroacetic acid → HCID 86703561, compound

HRID 1849690Notes

Reaction equation

HRID 1849690 reaction equation
[CH:1]1([C:4]2[C:5]([O:18][CH2:19][C:20]3([CH3:28])[CH2:27][CH2:26][C:23]4([CH2:25][CH2:24]4)[CH2:22][CH2:21]3)=[CH:6][C:7]([F:17])=[C:8]([CH:16]=2)[C:9]([O:11]C(C)(C)C)=[O:10])[CH2:3][CH2:2]1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>ClCCl>[CH:1]1([C:4]2[C:5]([O:18][CH2:19][C:20]3([CH3:28])[CH2:27][CH2:26][C:23]4([CH2:24][CH2:25]4)[CH2:22][CH2:21]3)=[CH:6][C:7]([F:17])=[C:8]([CH:16]=2)[C:9]([OH:11])=[O:10])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 86703560HCID 86703560, compound

Product 1

HCID 86703561HCID 86703561, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of tert-butyl 5-cyclopropyl-2-fluoro-4-((6-methylspiro[2.5]octan-6-yl)methoxy)benzoate (0.277 g, 0.713 mmol) and anisole (0.11 mL, 1.07 mmol) in dichloromethane (3 mL) was added trifluoroacetic acid (0.75 mL, 9.61 mmol). The reaction mixture was stirred at 0° C. for 4 hours before being quenched with water (5 mL). The reaction was diluted with dichloromethane (20 mL) and washed with water (4×10 mL) until the last wash was neutral as monitored by pH paper. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo to afford the title compound (0.213 g, 90%) as a white solid: MS (ES−) m/z 331.3 (M−1).

Workup

  1. custombefore being quenched with water (5 mL)
  2. additionThe reaction was diluted with dichloromethane (20 mL)
  3. washwashed with water (4×10 mL) until the
  4. washlast wash
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f8c8f75058f24194bb052defc48d5063
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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