Hydrochloric Acid → HCID 58934540, compound

HRID 855028Notes

Reaction equation

HRID 855028 reaction equation
[Cl:1][C:2]1[C:3]([O:22][CH3:23])=[C:4]([CH2:20][CH3:21])[CH:5]=[C:6]2[C:11]=1[O:10][CH:9]([C:12]([F:15])([F:14])[F:13])[C:8]([C:16]([O:18]C)=[O:17])=[CH:7]2.[OH-].[Li+].C(O)C.Cl>O1CCCC1.O>[Cl:1][C:2]1[C:3]([O:22][CH3:23])=[C:4]([CH2:20][CH3:21])[CH:5]=[C:6]2[C:11]=1[O:10][CH:9]([C:12]([F:15])([F:14])[F:13])[C:8]([C:16]([OH:18])=[O:17])=[CH:7]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 3939Lithium HydroxideHCID 69516328HCID 69516328, compound

Product 1

HCID 58934540HCID 58934540, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.14 g(0.4 mmol) of methyl 8-chloro-6-ethyl-7-methoxy-2-(trifluoromethyl)-2H-chromene-3-carboxylate in 5 mL of tetrahydrofuran was added a solution of 82 mg (1.95 mmol ) lithium hydroxide in 8 mL of water, followed by addition of 3 mL of ethanol. The resulting solution was heated to reflux for two h. The mixture was concd in vacuo. The residue was diluted with water and acidified to pH=1.0 with dilute hydrochloric acid. The product was extracted with ethyl acetate and the combinced organic extracts dried over anhydrous magnesium sulfate. Concentration in vacuo afforded 86 mg (64%) of a the product as white solid: 1H NMR (CDCl3/400 MHz) 7.80(s, 1H ), 7.01(s, 1H ), 5.77(q, J=6.8 Hz, 1H), 3.89(s, 3H), 2.62(q, J=7.6 Hz, 2H), 1.21(t, J=7.2 Hz, 3H). MS (ESI+) 337.0 (M+1, 100). MS(ES−) 335.0 (M−H, 100), HRMS (ES−) m/z calcd for (C14H11ClF3O4) M−H: 335.0292, found 335.0297.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for two h
  3. extractionThe product was extracted with ethyl acetate
  4. dry with materialthe combinced organic extracts dried over anhydrous magnesium sulfate
  5. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-63636840ab0a4c60bc39765207e36e91
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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