4-Toluenesulfonyl chloride → HCID 86672618, compound

HRID 2369270Notes

Reaction equation

HRID 2369270 reaction equation
C(N(CC)CC)C.[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1.Cl.CN(C)C.[CH3:24][C:25]([CH2:31][CH2:32][CH2:33][CH:34]([CH3:46])[CH2:35][CH2:36][CH2:37][CH:38]([CH3:45])[CH2:39][CH2:40][CH2:41][CH:42]([CH3:44])[CH3:43])=[CH:26][CH2:27][CH2:28][CH2:29][OH:30].CN(C)CCCN>C(Cl)Cl.CCCCCC.C(OCC)(=O)C>[CH3:24][C:25]([CH2:31][CH2:32][CH2:33][CH:34]([CH3:46])[CH2:35][CH2:36][CH2:37][CH:38]([CH3:45])[CH2:39][CH2:40][CH2:41][CH:42]([CH3:44])[CH3:43])=[CH:26][CH2:27][CH2:28][CH2:29][O:30][S:14]([C:11]1[CH:12]=[CH:13][C:8]([CH3:18])=[CH:9][CH:10]=1)(=[O:16])=[O:15]

Participants

8

Reactant 5

HCID 73974-Toluenesulfonyl chlorideHCID 7993N,N-Dimethyl-1,3-propanediamineHCID 8471TriethylamineHCID 10313079Trimethylamine HydrochlorideHCID 86672617HCID 86672617, compound

Product 1

HCID 86672618HCID 86672618, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Under a nitrogen atmosphere, 55 mL (0.39 mol) of triethylamine, 59.9 g (0.314 mol) of p-toluenesulfonyl chloride, and 2.5 g (26 mmol) of trimethylamine hydrochloride were added to a solution of 85.0 g (0.262 mol) of 5,9,13,17-tetramethyloctadec-4-en-1-ol in dry methylene chloride (0.26 L) at 0° C., sequentially. After being stirred for 1 hour, 9.9 mL (79 mmol) of N,N-dimethyl-1,3-propanediamine was added to the reaction solution at 0° C. After being stirred for 1 hour, the mixture was diluted with a mixed solvent of hexane/ethyl acetate. The resulting solution was washed with water, 3M hydrochloric acid (twice), saturated sodium bicarbonate aqueous solution, and saturated brine, successively, and dried over magnesium sulfate. After filtration, the filtrate was concentrated, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=90:10) to obtain 116 g of (5,9,13,17-tetramethyloctadec-4-enyl)tosylate (93% yield).

Workup

  1. stirringAfter being stirred for 1 hour
  2. washThe resulting solution was washed with water, 3M hydrochloric acid (twice), saturated sodium bicarbonate aqueous solution, and saturated brine
  3. dry with materialsuccessively, and dried over magnesium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated
  6. customthe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=90:10)

Sources & evidence

ORD record
ord-df97de11eae2416d93bda9b7af8f96b9
Source dataset
uspto-grants-2014_04
Patent number
US08703922B2

Reaction notes

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