Water → HCID 22841015, compound

HRID 414782Notes

Reaction equation

HRID 414782 reaction equation
[H-].[Na+].[CH2:3]([O:10][CH2:11][C@H:12]1[C@@H:17]([SH:18])[CH2:16][CH2:15][CH2:14][O:13]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[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>[CH2:3]([O:10][CH2:11][C@H:12]1[C@@H:17]([S:18][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])[CH2:16][CH2:15][CH2:14][O:13]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 82131-BromohexadecaneHCID 24758Sodium hydrideHCID 22841017HCID 22841017, compound

Product 1

HCID 22841015HCID 22841015, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
60 °C

Procedure

0.27 g of a 55% w/w suspension of sodium hydride in mineral oil was suspended in 2 ml of dimethylformamide. To the suspension was added dropwise a solution of 1.210 g of dl-cis-2-benzyloxymethyl-3-mercaptotetrahydropyran (prepared as described in Preparation 16) in 5 ml of dimethylformamide, whilst ice-cooling the mixture. The reaction mixture was stirred at 60° C. for 1 hour, after which it was cooled to room temperature. A solution of 1.86 g of hexadecyl bromide in 3 ml of dimethylformamide was then added, and the mixture was stirred at room temperature for 1 hour. It was then poured into water and extracted with ethyl acetate. The extract was washed with water, dried and concentrated by evaporation under reduced pressure. The resulting residue was subjected to column chromatography through 40 g of silica gel. The fraction eluted with mixtures of diethyl ether and hexane ranging from 3:97 to 10:90 by volume was collected to give 2.284 g of the title compound as a solid.

Workup

  1. temperaturewhilst ice-cooling the mixture
  2. temperatureafter which it was cooled to room temperature
  3. stirringthe mixture was stirred at room temperature for 1 hour
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. customdried
  7. concentrationconcentrated by evaporation under reduced pressure
  8. washThe fraction eluted with mixtures of diethyl ether and hexane ranging from 3:97 to 10:90 by volume
  9. customwas collected

Sources & evidence

ORD record
ord-68b5dec0ee18475fbfd8d0efed27e3cb
Source dataset
uspto-grants-1988_12
Patent number
US04794183

Reaction notes

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