Hydrochloric Acid → HCID 58934447, compound

HRID 854995Notes

Reaction equation

HRID 854995 reaction equation
C([O:3][C:4]([C:6]1[CH:7]([C:20]([F:23])([F:22])[F:21])[O:8][C:9]2[C:14]([CH:15]=1)=[CH:13][C:12]([Cl:16])=[CH:11][C:10]=2[C:17]#[C:18][CH3:19])=[O:5])C.C1COCC1.CCO.O.Cl>O>[Cl:16][C:12]1[CH:13]=[C:14]2[C:9](=[C:10]([C:17]#[C:18][CH3:19])[CH:11]=1)[O:8][CH:7]([C:20]([F:23])([F:21])[F:22])[C:6]([C:4]([OH:5])=[O:3])=[CH:15]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 18504229Ethanol tetrahydrofuran waterHCID 69517928HCID 69517928, compound

Product 1

HCID 58934447HCID 58934447, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To 0.320 g (1.01 mmole) of ethyl-6-chloro-8-prop-1-ynyl-2-(trifluoromethyl)-2H-chromene-3-carboxylate was added 5 mL of a solvent mixture of THF/EtOH/H2O (7:2:1) followed by 64 mg (1.52 mmole) of LiOH-H20. The mixture was stirred at 60° C. for two hours. The mixture was concd, treated with water and acidified with 0.5N HCl. The product precipitated out of solution and was washed three times with water. The resulting solid was dried to afford 0.050 g (16%) of a brown solid: 1H NMR (CDCl3/400 MHz) 1.83 (s,3H), 5.77 (q, 1H, J=6.8 Hz), 6.89 (d, 1H, J=2.4 Hz), 7.03 (d, 1H, J=2.4 Hz), 7.35 (s, 1H); MS (ES−) 315 (M−1, 100). HRMS (ES−) m/z calcd for (C14H8O3ClF3) 315.0030, found 315.0048.

Workup

  1. customThe product precipitated out of solution
  2. washwas washed three times with water
  3. customThe resulting solid was dried

Sources & evidence

ORD record
ord-fe160fbafa604d1dbd9418e7d54caf6f
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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