Lithium Hydroxide → HCID 63320442, compound

HRID 2040562Notes

Reaction equation

HRID 2040562 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:18]=[CH:17][C:9]([C:10]([O:12]CC3CC3)=[O:11])=[CH:8][C:7]=2[C:19]([F:22])([F:21])[F:20])[CH2:3][CH2:2]1.[Li+].[OH-]>C1COCC1.CO>[CH:1]1([CH2:4][O:5][C:6]2[CH:18]=[CH:17][C:9]([C:10]([OH:12])=[O:11])=[CH:8][C:7]=2[C:19]([F:20])([F:21])[F:22])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67220062HCID 67220062, compound

Product 1

HCID 63320442HCID 63320442, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of cyclopropylmethyl 4-(cyclopropylmethoxy)-3-(trifluoromethyl)benzoate (0.642 g, 2.043 mmol) in THF:MeOH (1:1, 10 mL) was added LiOH (1M, aq) (12.26 mmol). The reaction was stirred overnight, quenched with HCl (1M, aq) and extracted with EtOAc (twice). The combined extracts were dried over MgSO4 and concentrated to give the title compound as a white solid (0.502 g). LCMS m/z=261.1 [M+H]+. 1H NMR (400 MHz, CDCl3) δ ppm 0.39-0.46 (m, 2H), 0.62-0.71 (m, 2H), 1.23-1.38 (m, 1H), 4.03 (d, J=6.57 Hz, 2H), 7.02 (d, J=8.72 Hz, 1H), 8.23 (dd, J=8.72, 2.15 Hz, 1H), 8.34 (d, J=2.02 Hz, 1H).

Workup

  1. customquenched with HCl (1M, aq)
  2. extractionextracted with EtOAc (twice)
  3. dry with materialThe combined extracts were dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-43e97e1ce3744794b847db09b673e709
Source dataset
uspto-grants-2013_11
Patent number
US08580841B2

Reaction notes

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