Cesium fluoride → HCID 57360347, compound

HRID 1883230Notes

Reaction equation

HRID 1883230 reaction equation
[OH:1][CH2:2][CH:3]=[C:4]([C:6]1[CH:11]=[C:10]([CH:12]([CH3:14])[CH3:13])[CH:9]=[C:8]([CH:15]([CH3:17])[CH3:16])[C:7]=1[OH:18])[CH3:5].I[CH2:20][CH2:21][CH3:22].[F-].[Cs+]>CN(C=O)C.CCOC(C)=O>[CH:15]([C:8]1[C:7]([O:18][CH2:20][CH2:21][CH3:22])=[C:6]([C:4]([CH3:5])=[CH:3][CH2:2][OH:1])[CH:11]=[C:10]([CH:12]([CH3:14])[CH3:13])[CH:9]=1)([CH3:17])[CH3:16]

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 336431-IodopropaneHCID 69869174HCID 69869174, compound2×

Product 1

HCID 57360347HCID 57360347, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(3-hydroxy-1-methyl-propenyl)-4,6-diisopropyl-phenol (Intermediate 12, 1.82 g, 7.3 mmol) and 1-iodopropane (0.79 mL, 8.1 mmol) in DMF (20 mL) at room temperature was added CsF (3.9 g, 25.6 mmol). The reaction was stirred at room temperature for 1.5 h, diluted with EtOAc, washed successively with H2O, brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (10% EtOAc-hexanes) to yield the title compound as an off-white solid (2.06 g, 97%).

Workup

  1. washwashed successively with H2O, brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash column chromatography on silica gel (10% EtOAc-hexanes)

Sources & evidence

ORD record
ord-e259e8a894c2473b9426c7a61b213610
Source dataset
uspto-grants-2004_07
Patent number
US06759546B1

Reaction notes

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