Tetrahydrofuran → 2-(1-Phenylcyclopentyl)methyl-1,3-dithiane

HRID 1734904Notes

Reaction equation

HRID 1734904 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH2:7]([Li])[CH2:8][CH2:9][CH3:10].[S:12]1[CH2:17][CH2:16][CH2:15][S:14][CH2:13]1.[Cl-].[NH4+].O1CC[CH2:22][CH2:21]1>CN(C)P(=O)(N(C)C)N(C)C>[C:10]1([C:2]2([CH2:1][CH:13]3[S:14][CH2:15][CH2:16][CH2:17][S:12]3)[CH2:6][CH2:5][CH2:4][CH2:3]2)[CH:22]=[CH:21][CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 8058HexaneHCID 104511,3-DithianeHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

Product 1

HCID 199661182-(1-Phenylcyclopentyl)methyl-1,3-dithianeYield 51%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

720 μl of a 1.6M hexane solution of butyllithium were added dropwise at -78° C. to a solution of 126 mg (1.05 mmol) of 1,3-dithiane in a mixture of 1.5 ml of tetrahydrofuran and 720 μl of hexamethylphosphoric triamide, whilst stirring, and the resulting mixture was stirred for 10 minutes whilst cooling in an ice-salt bath. At the end of this time, a solution of 200 mg (0.699 mmol) of 2-(1-phenylcyclopentyl)methyl iodide [prepared as described in step (iii) above] in 1 ml of tetrahydrofuran was added dropwise to the mixture at -78° C. The resulting mixture was then stirred for 20 minutes, whilst cooling in an ice-salt bath. In order to stop the reaction, a saturated aqueous solution of ammonium chloride was then added to the reaction mixture, which was then extracted with diethyl ether. The extract was washed with a saturated aqueous solution of sodium chloride. The organic phase was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through 15 g of silica gel, using a 3:2 by volume mixture of hexane and methylene chloride as the eluent, to give 100 mg (yield 51%) of the title compound as a colorless foam-like material.

Workup

  1. stirringthe resulting mixture was stirred for 10 minutes
  2. temperaturewhilst cooling in an ice-salt bath
  3. stirringThe resulting mixture was then stirred for 20 minutes
  4. temperaturewhilst cooling in an ice-salt bath
  5. customthe reaction
  6. extractionwas then extracted with diethyl ether
  7. washThe extract was washed with a saturated aqueous solution of sodium chloride
  8. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  9. customthe solvent was removed by distillation under reduced pressure
  10. customThe resulting residue was purified by column chromatography through 15 g of silica gel
  11. additionby volume mixture of hexane and methylene chloride as the eluent

Sources & evidence

ORD record
ord-d40929a9af6a4871816b06c5b1d9d5d9
Source dataset
uspto-grants-1996_07
Patent number
US05534529

Reaction notes

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