Tetrabutylammonium Fluoride → HCID 17893978, compound

HRID 378223Notes

Reaction equation

HRID 378223 reaction equation
[CH3:1][CH:2]([C:12]1[C:20]2([CH3:21])[CH:15]([CH:16]([O:22][Si](C)(C)C)[CH2:17][CH2:18][CH2:19]2)[CH2:14][CH:13]=1)[CH2:3][C:4]#[C:5][C:6]([CH2:10][CH3:11])([OH:9])[CH2:7][CH3:8].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.O.[Cl-].[Na+].O>[CH3:1][CH:2]([C:12]1[C:20]2([CH3:21])[CH:15]([CH:16]([OH:22])[CH2:17][CH2:18][CH2:19]2)[CH2:14][CH:13]=1)[CH2:3][C:4]#[C:5][C:6]([CH2:10][CH3:11])([OH:9])[CH2:7][CH3:8]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 76481171HCID 76481171, compound

Product 1

HCID 17893978HCID 17893978, compoundYield 94.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 23713072Sodium chloride dihydrateSolvent

Procedure

To a stirred solution of 1.178 g (3.12 mmole) of [1(R*),3aR* (3aα,4β,7aβ)]-3a,4,5,6,7,7a-hexahydro-1-[1-methyl-5-ethyl-5-hydroxy-3-heptynyl)-7a-methyl-4-[(trimethylsilyl)oxy]-3H-indene in 15 ml anhydrous tetrahydrofuran was added 6 ml (6 mmole) of 1M tetrabutyl ammonium fluoride. The reaction mixture was stirred at room temperature overnight in an argon atmosphere. It was then diluted with 150 ml of water-brine 1:1 and extracted thoroughly with ethyl acetate. The combined extracts were washed with 2×30 ml water, dried over sodium sulfate and evaporated to dryness. The crude product was purified by FLASH chromatography to give 900 mg (94.5%) of the title compound, as a white crystalline solid.

Workup

  1. extractionextracted thoroughly with ethyl acetate
  2. washThe combined extracts were washed with 2×30 ml water
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness
  5. customThe crude product was purified by FLASH chromatography

Sources & evidence

ORD record
ord-bbee804fe6364c49898804fb5f1f3644
Source dataset
uspto-grants-2000_02
Patent number
US06030963

Reaction notes

Loading…