Water → HCID 123833212, compound

HRID 2369281Notes

Reaction equation

HRID 2369281 reaction equation
[H-].[Na+].[OH:3][CH2:4][C:5]([CH2:18][OH:19])([CH2:8][O:9][CH2:10][C:11]([CH2:16][OH:17])([CH2:14][OH:15])[CH2:12][OH:13])[CH2:6][OH:7].[CH3:20][C:21]([CH2:37][CH2:38][CH2:39][CH:40]([CH3:52])[CH2:41][CH2:42][CH2:43][CH:44]([CH3:51])[CH2:45][CH2:46][CH2:47][CH:48]([CH3:50])[CH3:49])=[CH:22][CH2:23][CH2:24][CH2:25]OS(C1C=CC(C)=CC=1)(=O)=O.O>CN(C)C=O>[CH3:20][C:21]([CH2:37][CH2:38][CH2:39][CH:40]([CH3:52])[CH2:41][CH2:42][CH2:43][CH:44]([CH3:51])[CH2:45][CH2:46][CH2:47][CH:48]([CH3:50])[CH3:49])=[CH:22][CH2:23][CH2:24][CH2:25][O:13][CH2:12][C:11]([CH2:16][OH:17])([CH2:10][O:9][CH2:8][C:5]([CH2:18][OH:19])([CH2:6][OH:7])[CH2:4][OH:3])[CH2:14][OH:15]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 31352DipentaerythritolHCID 86672618HCID 86672618, compound

Product 1

HCID 123833212HCID 123833212, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

0.37 g (60%, 9.2 mmol) of sodium hydride was added to a solution of 2.35 g (9.24 mmol) of dipentaerythritol in dry N,N-dimethylformamide (6 mL) with cooling on ice. After the mixture was stirred for 1 hour at 50° C., the above (5,9,13,17-tetramethyloctadec-4-enyl)tosylate was added dropwise thereto, with additional stirring for 20 hours at 60° C. After addition of water at 0° C., the reaction mixture was extracted with ethyl acetate. The extract was washed with water, 1M hydrochloric acid, saturated sodium bicarbonate aqueous solution, and saturated brine, successively, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated, and the resulting residue was purified by silica gel column chromatography (methanol/methylene chloride mixture) to obtain 494 mg of the title compound (19% yield in 2 steps) as a white solid. The results of NMR analysis of the thus obtained compound are as shown below.

Workup

  1. temperaturewith cooling on ice
  2. stirringwith additional stirring for 20 hours at 60° C
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe extract was washed with water, 1M hydrochloric acid, saturated sodium bicarbonate aqueous solution, and saturated brine
  5. dry with materialsuccessively, and dried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated
  8. customthe resulting residue was purified by silica gel column chromatography (methanol/methylene chloride mixture)

Sources & evidence

ORD record
ord-995ed2b9f83c41d7993d8a79d23a7160
Source dataset
uspto-grants-2014_04
Patent number
US08703922B2

Reaction notes

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