4-Toluenesulfonyl chloride → HCID 66818580, compound

HRID 1755057Notes

Reaction equation

HRID 1755057 reaction equation
C([Li])CCC.[CH2:6]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([CH3:28])([CH2:26][OH:27])[CH2:24]O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.S(Cl)(C1C=CC(C)=CC=1)(=O)=O>C1COCC1.CCOCC.O>[CH2:6]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]1([CH3:28])[CH2:26][O:27][CH2:24]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 66817626HCID 66817626, compoundHCID 178418339Butyllithium2×

Product 1

HCID 66818580HCID 66818580, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

n-Butyllithium (2.6 M solution in hexane, 0.295 ml, 0.767 mmol) was added to a solution of 2-(9-benzyloxy-nonyl)-2-methyl-propane-1,3-diol (221 mg, 0.686 mmol) in THF (5.1 ml) at 0° C. over three minutes, and the mixture was then stirred at the same temperature for 30 minutes. A solution of TsCl (138 mg, 0.723 mmol) in THF (0.91 ml) was added to the reaction solution at 0° C. over eight minutes, and the mixture was then stirred at the same temperature for one hour. n-Butyllithium (2.6 M solution in hexane, 0.295 ml, 0.767 mmol) was added dropwise to the reaction mixture at 0° C., and the mixture was then stirred at 60° C. for six hours. The reaction mixture was diluted with ether and water was then added, followed by extraction with ether. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=15/1) to give 3-(9-benzyloxy-nonyl)-3-methyl-oxetane (188 mg, 90%).

Workup

  1. stirringthe mixture was then stirred at the same temperature for one hour
  2. stirringthe mixture was then stirred at 60° C. for six hours
  3. additionwas then added
  4. extractionfollowed by extraction with ether
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=15/1)

Sources & evidence

ORD record
ord-3e73ecd6a699460ebca9996b48b095d7
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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