(Diethylamino)sulfur trifluoride → HCID 21459479, compound

HRID 1941038Notes

Reaction equation

HRID 1941038 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH:11]2[CH2:16][CH2:15][CH:14]([CH:17]3[CH2:22][CH2:21][CH:20]([CH2:23][CH2:24][CH2:25]O)[CH2:19][CH2:18]3)[CH2:13][CH2:12]2)=[CH:5][CH:4]=1.C(N(S(F)(F)[F:35])CC)C>C(COC)OC>[F:35][CH2:25][CH2:24][CH2:23][CH:20]1[CH2:21][CH2:22][CH:17]([CH:14]2[CH2:15][CH2:16][CH:11]([CH2:10][CH2:9][C:6]3[CH:7]=[CH:8][C:3]([C:2]([F:28])([F:27])[F:1])=[CH:4][CH:5]=3)[CH2:12][CH2:13]2)[CH2:18][CH2:19]1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 21459451HCID 21459451, compound

Product 1

HCID 21459479HCID 21459479, compoundYield 49.5%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Dimethoxyethane (10 ml) was added to the above 3-(4-(4-(2-(4-trifluoromethylphenyl)ethyl)cyclohexyl)cyclohexyl)propanol (1.20 g, 3.03 mmol), followed by dropwise adding thereto diethylaminosulfur trifluoride (DAST) (1.13 g, 7.01 mmol), refluxing the mixture for 5 hours, extracting the resulting product with toluene, washing the organic layer successively with a saturated, aqueous solution of sodium bicarbonate and water, drying over magnesium sulfate, distilling off the solvent, purifying the residue according to column chromatography treatment using heptane as a developing solvent, on silica gel, distilling off the solvent, and recrystallizing the residue from ethanol/heptane (9/1), to isolate only trans-form of 1-(2-(4-(4-(3-fluoropropyl)cyclohexyl)cyclohexyl)ethyl)-4-trifluoromethylbenzene (0.60 g, 1.5 mmol). Yield: 49.5%. SB -I point: 118.9° C.

Workup

  1. additionby dropwise adding
  2. extractionextracting the resulting product with toluene
  3. washwashing the organic layer successively with a saturated, aqueous solution of sodium bicarbonate and water
  4. dry with materialdrying over magnesium sulfate
  5. distillationdistilling off the solvent
  6. custompurifying the residue
  7. distillationon silica gel, distilling off the solvent
  8. customrecrystallizing the residue from ethanol/heptane (9/1)

Sources & evidence

ORD record
ord-4ccc0c7b3cb24cd1a3a9a93dc45475dd
Source dataset
uspto-grants-1997_12
Patent number
US05702641

Reaction notes

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