Tetrahydrofuran → HCID 22641075, compound

HRID 2415234Notes

Reaction equation

HRID 2415234 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([OH:17])[CH:8]=1)(C)C.C1COCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O>[C:6]([C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([OH:17])[CH:8]=1)#[CH:5]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 22641103Methyl 2-hydroxy-4-trimethylsilylethynylbenzoate

Product 1

HCID 22641075HCID 22641075, compoundYield 113.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3.07 g (12.4 mmol) of methyl 4-trimethylsilanylethynyl-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-713b407ec169475490a5253892e08dca
Source dataset
uspto-grants-2004_11
Patent number
US06818666B2

Reaction notes

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