Water → HCID 22841026, compound

HRID 414775Notes

Reaction equation

HRID 414775 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-benzyloxymethyl-3-hydroxytetrahydropyran (prepared as described in Preparation 6) in 10 ml of dimethylformamide was added dropwise, with ice-cooling, to 10 ml of dimethylformamide containing suspended in it 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 extract was washed with water, dried and condensed by evaporation under reduced pressure. The oily residue was subjected to column chromatography resulting through 100 g of silica gel. The fraction 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, melting at 28.5°-29.5° C. (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 extract was washed with water
  6. customdried
  7. customcondensed
  8. customby evaporation under reduced pressure
  9. customresulting through 100 g of silica gel
  10. washThe fraction eluted with mixtures of diethyl ether and hexane ranging from 1:20 to 1:10 by volume

Sources & evidence

ORD record
ord-c3c50a4bb2c543bc8c256868d4d7db7a
Source dataset
uspto-grants-1988_12
Patent number
US04794183

Reaction notes

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