Water → HCID 86621303, compound

HRID 914486Notes

Reaction equation

HRID 914486 reaction equation
[CH2:1]([O:5][CH2:6][CH2:7][CH2:8]O)[CH2:2][CH2:3][CH3:4].C(N(CC)CC)C.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.[OH2:28]>ClCCl.CN(C)C1C=CN=CC=1>[CH2:1]([O:5][CH2:6][CH2:7][CH2:8][C:21]1[CH:22]=[C:17]([CH3:27])[CH:18]=[CH:19][C:20]=1[S:23]([OH:28])(=[O:25])=[O:24])[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 824573-Butoxy-1-propanol

Product 1

HCID 86621303HCID 86621303, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

3-Butoxy propan-1-ol (3.15 g) synthesized in Reference Example 44 was dissolved in dichloromethane (80 mL), triethylamine (6.6 mL), p-toluenesulfonyl chloride (6.82 g) and 4-dimethylaminopyridine (0.29 g) 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=3:1) to give the title compound (4.46 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=3:1)

Sources & evidence

ORD record
ord-197bbb8deda24221b91ae9278eaadb51
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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