Tetrabutylammonium Fluoride → 4-Hydroxy-4-methyl-pent-2-ynoic acid ethyl ester

HRID 237845Notes

Reaction equation

HRID 237845 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5]#[C:6][C:7]([CH3:14])([O:9][Si](C)(C)C)[CH3:8])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C(OCC)C>[CH2:1]([O:3][C:4](=[O:15])[C:5]#[C:6][C:7]([OH:9])([CH3:8])[CH3:14])[CH3:2]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 866402384-Methyl-4-trimethylsilanyloxy-pent-2-ynoic acid ethyl ester

Product 1

HCID 112289264-Hydroxy-4-methyl-pent-2-ynoic acid ethyl esterYield 94.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 4-methyl-4-trimethylsilanyloxy-pent-2-ynoic acid ethyl ester (5.4 g, 23.7 mmol) in ethyl ether (50 mL) was added tetrabutylammonium fluoride (TBAF) (7.42 g, 28.4 mmol). The reaction mixture was stirred at room temperature for 2 hours, quenched with H2O, and extracted with ethyl ether. The organic phase was washed with brine, dried (Na2SO4) and concentrated to afford 3.51 g of 4-hydroxy-4-methyl-pent-2-ynoic acid ethyl ester as yellow oil.

Workup

  1. customquenched with H2O
  2. extractionextracted with ethyl ether
  3. washThe organic phase was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-29ed6ef72ce0488699e38aa90154baa0
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Reaction notes

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