Cesium carbonate → HCID 22392771, compound

HRID 1071385Notes

Reaction equation

HRID 1071385 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11]C)=[O:10])=[CH:4][CH:3]=1.Cl[CH2:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=[C:17]([CH3:25])[CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.[I-].[Na+]>[CH3:25][C:17]1[CH:16]=[C:15]([CH2:14][O:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:6][CH:7]=2)[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl esterHCID 115357194-(Chloromethyl)-2-methylquinoline

Product 1

HCID 22392771HCID 22392771, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl (4-hydroxyphenyl)acetate (10.0 g, 60.2 mmol) in 400 mL THF was added 4-chloromethyl-2-methylquinoline (11.5 g, 60.2 mmol), cesium carbonate (29.4 g, 90.3 mmol), and sodium iodide (451 mg, 3 mmol). The reaction was heated to reflux for 72 hr, after which the reaction was extracted from sat KH2PO4 with EtOAc×3. The combined organic layers were dried with MgSO4, filtered, and concentrated. This residue was taken up in 200 mL MeOH and treated with 1 M NaOH (100 mL) for 16 hr. The reaction was treated with dilute KH2PO4 and EtOAc. A solid formed between the layers that was filtered through a sintered glass funnel and recrystallized from EtOH/water to give 14 g (76%) of the product acid. MS found: (M+H)=308.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 72 hr
  3. extractionafter which the reaction was extracted
  4. dry with materialThe combined organic layers were dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. additiontreated with 1 M NaOH (100 mL) for 16 hr
  8. additionThe reaction was treated with dilute KH2PO4 and EtOAc
  9. customA solid formed between the layers that
  10. filtrationwas filtered through a sintered glass funnel
  11. customrecrystallized from EtOH/water

Sources & evidence

ORD record
ord-5fb6ec1aafb4442a8979db4b8a48ebcd
Source dataset
uspto-grants-2005_06
Patent number
US06906053B2

Reaction notes

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