Water → HCID 22841026, compound

HRID 329512Notes

Reaction equation

HRID 329512 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]1[C@H:15]([OH:16])[CH2:14][CH2:13][CH2:12][O:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:19](Br)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34].O>CN(C)C=O>[CH2:1]([O:8][CH2:9][C@H:10]1[C@H:15]([O:16][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH3:19])[CH2:14][CH2:13][CH2:12][O:11]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 82131-BromohexadecaneHCID 24758Sodium hydrideHCID 13982256HCID 13982256, compound

Product 1

HCID 22841026HCID 22841026, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 2.22 g of dl-trans-2-benzyloxymethyltetrahydropyran-3-ol (prepared as described in Preparation 2) in 10 ml of dimethylformamide was added dropwise, with ice-cooling, to 10 ml of dimethylformamide containing 0.480 g of a 55% w/w suspension of sodium hydride in mineral oil. The reaction mixture was stirred at room temperature for 60 minutes, after which 5.49 g of hexadecyl bromide were added, and the resulting mixture was stirred for a further 4 hours. Finally, the mixture was stirred at 60° C. for 60 minutes and then cooled. It was then poured into 100 ml of water, and extracted twice with ethyl acetate. The combined extracts were washed with water, dried over anhydrous magnesium sulfate and condensed by evaporation under reduced pressure. The resulting oily residue was subjected to column chromatography through 100 g of silica gel. Those fractions eluted with mixtures of diethyl ether and hexane ranging from 1:20 to 1:10 by volume gave 3.82 g of the title compound as a solid having a low melting point, i.e. 28.5°-29.5° C. (after recrystallization from cold methanol).

Workup

  1. stirringthe resulting mixture was stirred for a further 4 hours
  2. stirringFinally, the mixture was stirred at 60° C. for 60 minutes
  3. temperaturecooled
  4. extractionextracted twice with ethyl acetate
  5. washThe combined extracts were washed with water
  6. dry with materialdried over anhydrous magnesium sulfate and condensed by evaporation under reduced pressure
  7. washThose fractions eluted with mixtures of diethyl ether and hexane ranging from 1:20 to 1:10 by volume

Sources & evidence

ORD record
ord-47babf98dd34402f8d076ff144d4b742
Source dataset
uspto-grants-1990_01
Patent number
US04891363

Reaction notes

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