Water → HCID 14369504, compound

HRID 414780Notes

Reaction equation

HRID 414780 reaction equation
[CH2:1]([OH:7])[C:2]1[O:6][CH2:5][CH2:4][CH:3]=1.[H-].[Na+].[CH2:10](Br)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].O>CN(C)C=O>[CH2:25]([O:7][CH2:1][C:2]1[O:6][CH2:5][CH2:4][CH:3]=1)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 82131-BromohexadecaneHCID 24758Sodium hydrideHCID 14206225HCID 14206225, compound

Product 1

HCID 14369504HCID 14369504, compoundYield 71.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 4.09 g of 4,5-dihydrofurfuryl alcohol (prepared as described in Preparation 12) in 10 ml of dimethylformamide was added dropwise to 2.62 g of a 55% w/w suspension of sodium hydride in mineral oil, itself suspended in 40 ml of dimethylformamide, whilst maintaining the temperature of the mixture at from 5° to 12° C. by ice-cooling. The mixture was then stirred at room temperature for 30 minutes, 18.32 g of hexadecyl bromide were added to the solution, and the whole was stirred at room temperature for 15 hours. The reaction mixture was then poured into 200 ml of water, and extracted twice with diethyl ether. The extract was washed with water, dried and condensed by evaporation under reduced pressure. The oily residue, 17 g, was subjected to column chromatography through 400 g of Grade II-III alumina (a product of Woelm Pharma, West Germany). The fraction eluted with a 1:20 by volume mixture of diethyl ether and hexane gave 9.512 g of the title compound as a solid, melting at 30.5°-31.5° C. (cold hexane).

Workup

  1. temperaturewhilst maintaining the temperature of the mixture at from 5° to 12° C. by ice-
  2. temperaturecooling
  3. stirringthe whole was stirred at room temperature for 15 hours
  4. extractionextracted twice with diethyl ether
  5. washThe extract was washed with water
  6. customdried
  7. customcondensed
  8. customby evaporation under reduced pressure
  9. washThe fraction eluted with a 1:20 by volume mixture of diethyl ether and hexane

Sources & evidence

ORD record
ord-48607985ef5b4940bf84316718f0676d
Source dataset
uspto-grants-1988_12
Patent number
US04794183

Reaction notes

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