Water → HCID 86621304, compound

HRID 914489Notes

Reaction equation

HRID 914489 reaction equation
[CH:1]1([O:7][CH2:8][CH2:9][CH2:10]O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.[OH2:30]>ClCCl.CN(C)C1C=CN=CC=1>[CH:1]1([O:7][CH2:8][CH2:9][CH2:10][C:23]2[CH:24]=[C:19]([CH3:29])[CH:20]=[CH:21][C:22]=2[S:25]([OH:30])(=[O:27])=[O:26])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 100348783-(cyclohexyloxy)propan-1-ol

Product 1

HCID 86621304HCID 86621304, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

3-(Cyclohexyloxy)propan-1-ol (820 mg) synthesized in Reference Example 47 was dissolved in dichloromethane (20 mL), triethylamine (1.1 mL), p-toluenesulfonyl chloride (1.2 g) and 4-dimethylaminopyridine (63 mg) were added thereto, and the mixture was stirred at room temperature overnight. Water was added to the reaction solution, and the organic layer was separated and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=5:1) to give the title compound (1.0 g) as a colorless oil.

Workup

  1. customthe organic layer was separated
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-b2b2d4eabd1a4541bbe597fd0f1b47d1
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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