Methanol → HCID 67513377, compound

HRID 1519544Notes

Reaction equation

HRID 1519544 reaction equation
C[O:2][C:3](=[O:18])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[N:12])=[C:7]([O:13][C:14]([F:17])([F:16])[F:15])[CH:6]=1.C1COCC1.CO.O[Li].O>O>[C:11]([C:8]1[CH:9]=[CH:10][C:5]([CH2:4][C:3]([OH:18])=[O:2])=[CH:6][C:7]=1[O:13][C:14]([F:15])([F:17])[F:16])#[N:12]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 86694459HCID 86694459, compound

Product 1

HCID 67513377HCID 67513377, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of methyl(4-cyano-3-trifluoromethoxyphenyl)acetate (2.15 g, 8.3 mmol) in 1:1 THF:MeOH (10 mL each) was added LiOH—H2O (0.42 g, 10.0 mmol) in water (30 mL). The reaction mixture was stirred at room temperature for 12 hours at which time the starting ester was consumed by TLC (25% ethyl acetate/hexanes). The mixture was concentrated in vacuo and acidified to pH<3 by dropwise addition of 12N HCl. The acidified solution was then extracted with ethyl acetate, dried over sodium sulfate and concentrated in vacuo to yield the crude title product. LC-MS (IE, m/z): 246 [M+1]+. 1H-NMR (500 MHz, CDCl3) δ ppm 3.81 (s, 2H), 7.39 (d, J=7.5 Hz, 1H), 7.40 (s, 1H), 7.75 (d, J=7.5 Hz, 1H).

Workup

  1. customwas consumed by TLC (25% ethyl acetate/hexanes)
  2. concentrationThe mixture was concentrated in vacuo
  3. additionacidified to pH<3 by dropwise addition of 12N HCl
  4. extractionThe acidified solution was then extracted with ethyl acetate
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6868c10729664b369ff0f1dd649e729d
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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