Tetrabutylammonium Fluoride → HCID 69545342, compound

HRID 1169185Notes

Reaction equation

HRID 1169185 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-951976ce406249fc9c5a45ce4ec9fcf0
Source dataset
uspto-grants-2003_09
Patent number
US06627763B2

Reaction notes

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