Lithium Hydroxide → HCID 11775436, compound

HRID 854989Notes

Reaction equation

HRID 854989 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[O:19][CH:18]([C:23]([F:26])([F:25])[F:24])[C:17]([C:27]([O:29]CC)=[O:28])=[CH:16]3)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[OH-].[Li+]>O>[F:11][C:9]([F:10])([F:12])[C:7]1[CH:6]=[C:5]([C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[O:19][CH:18]([C:23]([F:24])([F:25])[F:26])[C:17]([C:27]([OH:29])=[O:28])=[CH:16]3)[CH:4]=[C:3]([C:2]([F:1])([F:32])[F:33])[CH:8]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86599476HCID 86599476, compound

Product 1

HCID 11775436HCID 11775436, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the solution of 150 mg (0.31 mmol) of ethyl 6-[3,5-bis(trifluoromethyl)phenyl]-2-(trifluoromethyl)-2H-chromene-3-carboxylate in 5 mL of tetrahydrofliran was added a solution of 51 mg (1.24 mmol) of lithium hydroxide (LiOH.2H2O) in 5 mL of water. The resulting mixture was heated to reflux for one hr. After cooling to room temperature, the volatiles were removed. The residue was diluted with water, then acidified at 0° C. with dilute hydrochloric acid to pH=1.5. The product was then extracted with ethyl ether. The combined organic extracts were dried over anhydrous magnesium sulfate. Evaporation of the dried organic solution afforded 0.13 g (92%) of a light yellow solid: 1H NMR (CDCl3/400 MHz) 7.89(s, 2H), 7.78(s, 1H), 7.77(s, 1H), 7.51(dd, J=2.4 Hz, 8.4 Hz, 1H), 7.41(d, J=2.4Hz, 1 H), 7.06(d, J=8.4 Hz, 1H), 5.69(m, 1H). MS (ES+) 457.0(M+1, 100).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for one hr
  3. customthe volatiles were removed
  4. additionThe residue was diluted with water
  5. customacidified at 0° C. with dilute hydrochloric acid to pH=1.5
  6. extractionThe product was then extracted with ethyl ether
  7. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  8. customEvaporation of the dried organic solution

Sources & evidence

ORD record
ord-9150c35d99dc4b5592392ff2fd6de799
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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