Tetrahydrofuran → HCID 22641075, compound

HRID 1532293Notes

Reaction equation

HRID 1532293 reaction equation
C[Si](C)(C)[C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([OH:13])[C:4]=1C#C.[CH2:18]1COC[CH2:19]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O>[C:18]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([OH:13])[CH:4]=1)#[CH:19]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 86756539HCID 86756539, compound

Product 1

HCID 22641075HCID 22641075, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3.07 g (12.4 mmol) of methyl 4-trimethylsilanyl-ethynyl-2-hydroxybenzoate are mixed, in a 500 ml three-necked flask, with 50 ml of THF, and 13.7 ml of a tetrabutylammonium fluoride solution (1 M/THF) are added dropwise. The reaction medium is stirred for 1 h at room temperature and is then poured into water and extracted with ethyl ether. After separation of the phases by settling, the organic phase is dried over magnesium sulphate and concentrated. 2.48 g (100%) of a beige-coloured powder are obtained. m.p.=62° C.

Workup

  1. additionare added dropwise
  2. extractionextracted with ethyl ether
  3. customAfter separation of the phases
  4. dry with materialthe organic phase is dried over magnesium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8130659e125c4588a2e9ffd422dda9e7
Source dataset
uspto-grants-2001_03
Patent number
US06201019B1

Reaction notes

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