Lithium hydroxide, monohydrate → HCID 58934724, compound

HRID 855014Notes

Reaction equation

HRID 855014 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[O:8][CH:7]([C:14]([F:17])([F:16])[F:15])[C:6]([C:18]([O:20]CC)=[O:19])=[CH:5]2.O.[OH-].[Li+]>O1CCCC1.O>[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[O:8][CH:7]([C:14]([F:17])([F:15])[F:16])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 58934593HCID 58934593, compound

Product 1

HCID 58934724HCID 58934724, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To the solution of 3.0 g (7.0 mmol) of ethyl 6-iodo-7-methoxy-2-(trifluoromethyl)-2H-chromene-3-carboxylate in 50 mL of tetrahydrofuran was added a solution of 1.2 g (28 mmol) of lithium hydroxide hydrate in 55 mL of water. The resulting solution was heated to reflux for four hr. The volatiles were removed. The residue was diluted with water. The resulting solution was acidified at 0° .C with dilute hydrochloric acid to pH=1.5. The product was extracted with ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate, filtered and concd to afford 2.5 g (81%) of a light yellow solid: 1H NMR (CDCl3/400 MHz) 7.56(s, 1H), 7.52(s, 1H), 6.42(s, 1H), 5.60(q, J=6.8 Hz, 1H), 3.81 (s, 3H). MS (ESI+) 400.9 (M+1, 100). MS(ES−) 398.9(M−H, 100). HRMS (ES−) m/z calcd for (C12H7F3O4) M−H: 398.9336, found 398.9359.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for four hr
  3. customThe volatiles were removed
  4. additionThe residue was diluted with water
  5. customwas acidified at 0°
  6. extractionThe product was extracted with ethyl acetate
  7. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  8. filtrationfiltered

Sources & evidence

ORD record
ord-a7808769c8e64f3f8b966c31dfb280ad
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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