Hydrochloric Acid → HCID 178515105, compound

HRID 410015Notes

Reaction equation

HRID 410015 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:27])[C:7]([CH:16]3[CH2:21][CH2:20][CH:19]([C:22]([O:24]CC)=[O:23])[CH2:18][CH2:17]3)=[C:8]([C:12]([F:15])([F:14])[F:13])[O:9]2)=[CH:4][CH:3]=1.Cl>O1CCOCC1>[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:27])[C:7]([C@H:16]3[CH2:17][CH2:18][C@H:19]([C:22]([OH:24])=[O:23])[CH2:20][CH2:21]3)=[C:8]([C:12]([F:15])([F:13])[F:14])[O:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67367261HCID 67367261, compound

Product 1

HCID 178515105HCID 178515105, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of ethyl 4-(7-hydroxy-4-oxo-2-(trifluoromethyl)-4H-chromen-3-yl)cyclohexanecarboxylate (450 mg, 1.1 mmol) in dioxane (3 ml) was added conc. HCl (3 ml). The solution was stirred at 75° C. overnight. The mixture was concentrated in vacuo to give a yellow solid, which was purified by prep-HPLC to afford the pure trans isomer, the desired product in Example 3 (100 mg, 24%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customto give a yellow solid, which
  3. customwas purified by prep-HPLC
  4. customto afford the pure trans isomer

Sources & evidence

ORD record
ord-c18f891b06d341ea959bd5df6d6608f8
Source dataset
uspto-grants-2014_06
Patent number
US08759548B2

Reaction notes

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