Cesium fluoride → 3-Methoxyquinoxalin-5-ol

HRID 1437375Notes

Reaction equation

HRID 1437375 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[N:11][C:10]2[C:5](=[C:6]([O:13][Si](C(C)C)(C(C)C)C(C)C)[CH:7]=[CH:8][CH:9]=2)[N:4]=1.[F-].[Cs+]>O1CCCC1.CO>[CH3:1][O:2][C:3]1[CH:12]=[N:11][C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([OH:13])[C:5]=2[N:4]=1

Participants

4

Reactant 2

HCID 25953Cesium fluorideHCID 686959212-Methoxy-8-triisopropylsilanyloxy-quinoxaline

Product 1

HCID 1362623933-Methoxyquinoxalin-5-olYield 113.5%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of (d) (6.95 g, 21 mmol) in tetrahydrofuran/methanol (280 ml/140 ml) was treated with caesium fluoride (4.73 g, 31.4 mmol) and stirred for 18 hours. The mixture was evaporated and the residue partitioned between diethyl ether and dilute aqueous hydrochloric acid. The aqueous phase was further extracted with diethyl ether and the combined extracts dried and evaporated to give an oil (4.2 g).

Workup

  1. customThe mixture was evaporated
  2. customthe residue partitioned between diethyl ether and dilute aqueous hydrochloric acid
  3. extractionThe aqueous phase was further extracted with diethyl ether
  4. customthe combined extracts dried
  5. customevaporated

Sources & evidence

ORD record
ord-e352872d5e004c98b4fdadc92c7b0840
Source dataset
uspto-grants-2009_11
Patent number
US07622481B2

Reaction notes

Loading…