Dichloromethane → HCID 22375180, compound

HRID 1956094Notes

Reaction equation

HRID 1956094 reaction equation
[CH2:1]([CH:4]1[CH2:9][CH2:8][CH:7]([CH:10]2[CH2:15][CH2:14][CH:13]([O:16][CH2:17][CH2:18][CH2:19]O)[CH2:12][CH2:11]2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].CCN(S(F)(F)[F:27])CC.ClCCl>C1(C)C=CC=CC=1>[CH2:1]([CH:4]1[CH2:9][CH2:8][CH:7]([CH:10]2[CH2:15][CH2:14][CH:13]([O:16][CH2:17][CH2:18][CH2:19][F:27])[CH2:12][CH2:11]2)[CH2:6][CH2:5]1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 123472(Diethylamino)sulfur trifluorideHCID 22375168HCID 22375168, compound

Product 1

HCID 22375180HCID 22375180, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2.75 g (9.8 mmol) of 4-(4-propylcyclohexyl)-(3-hydroxypropyloxy)cyclohexane obtained in Example 4, 3.14 g (19.6 mmol) of DAST, and 25 ml of dichloromethane was stirred for 5 hours at a room temperature. The reaction product was put in 40 ml of an ice water and extracted with 40 ml of toluene. The organic layer was washed with water twice and dried over anhydrous magnesium sulfate. The magnesium sulfate was separated, the solvent was distilled off under a reduced pressure, and the residue thus obtained was subjected to a silica gel column chromatography (eluate: toluene) to obtain 1.87 g of a crude 4-(4-propylcyclohexyl)-(3-fluoropropyloxy) cyclohexane. This product was recrystallized twice from 6 ml of ethanol in a freezer to obtain 1.60 g (yield 58%) of 4-(4-propylcyclohexyl)-(3-fluoropropyloxy)cyclohexane. Several kinds of spectra well supported its structure.

Workup

  1. extractionextracted with 40 ml of toluene
  2. washThe organic layer was washed with water twice
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe magnesium sulfate was separated
  5. distillationthe solvent was distilled off under a reduced pressure
  6. customthe residue thus obtained

Sources & evidence

ORD record
ord-9511f9aa036d4f95b7ae737a6cae9ff7
Source dataset
uspto-grants-1998_07
Patent number
US05779936

Reaction notes

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