Tetrabutylammonium Fluoride → HCID 69545342, compound

HRID 2304962Notes

Reaction equation

HRID 2304962 reaction equation
[CH2:1]([O:7][C:8]([CH2:10][CH2:11][CH:12]([O:18][C:19](=[O:36])[CH:20]=[CH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[O:28][Si](C(C)(C)C)(C)C)[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[O:9])[CH2:2][CH:3]=[CH:4][CH2:5][CH3:6].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH2:1]([O:7][C:8]([CH2:10][CH2:11][CH:12]([O:18][C:19](=[O:36])/[CH:20]=[CH:21]/[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[OH:28])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[O:9])[CH2:2]/[CH:3]=[CH:4]\[CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69545291HCID 69545291, compound

Product 1

HCID 69545342HCID 69545342, compoundYield 10.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6.14 g 3-[2-(tert-butyl-dimethyl-silanyloxy)-phenyl]-acrylic acid 1-(2-hex-3-enyloxycarbonyl-ethyl)-hexyl ester in 50 ml of tetrahydrofuran, a solution of 25 ml of a 1M tetrabutylammoniumfluoride solution was added at 0° C. After stirring at room temperature for 90 minutes, the solution was quenched with water and extracted with ether. The organic phase was washed with water, dried and evaporated to dryness. The residue was purified by Kugelrohr-distillation and chromatography to yield 0.51 g of a colorless oil.

Workup

  1. customthe solution was quenched with water
  2. extractionextracted with ether
  3. washThe organic phase was washed with water
  4. customdried
  5. customevaporated to dryness
  6. distillationThe residue was purified by Kugelrohr-distillation and chromatography

Sources & evidence

ORD record
ord-abf3bcd4c2574d3a87b0a4febd2bbc7f
Source dataset
uspto-grants-2002_08
Patent number
US06437150B1

Reaction notes

Loading…