1-Iodooctadecane → HCID 20218649, compound

HRID 235712

Reaction equation

HRID 235712 reaction equation
[OH:1][CH2:2][CH:3]([NH:12][C:13](=[O:15])[CH3:14])[CH2:4][O:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][O:7]1.[H-].[Na+].[CH2:18](I)[CH2:19][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][CH2:34][CH3:35]>CN(C)C=O.O1CCCC1.CCOCC>[CH2:35]([O:1][CH2:2][CH:3]([NH:12][C:13](=[O:15])[CH3:14])[CH2:4][O:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][O:7]1)[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][CH2:19][CH3:18]

Participants

7

Reactant 3

HCID 124021-IodooctadecaneHCID 24758Sodium hydrideHCID 20219052N-[1-(hydroxymethyl)-2-[(tetrahydro-2H-pyran-2-yl)oxy]ethyl]acetamide

Product 1

HCID 20218649HCID 20218649, compoundYield 34.1%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of about 10.85 g of N-[1-(hydroxymethyl)-2-[(tetrahydro-2H-pyran-2-yl)oxy]ethyl]acetamide in about 240 ml of dry dimethylformamide was added dropwise to a suspension of about 3.12 g of about 50% sodium hydride (pre-washed with anhydrous ether). After stirring about one hour a solution of about 22.8 g of octadecyl iodide in about 150 ml of tetrahydrofuran was added, stirring was continued for about 24 hours, then the mixture was diluted with ether and washed with a minimum amount of brine. The organic layer was dried, the solvents evaporated and the crude material purified by chromatography on silica gel, eluting with ethyl acetate:hexane:ethanol (about 1:1:0.2), giving about 8 g of the desired title compound, mp 52°-55° C.

Workup

  1. additionwas added
  2. washwashed with a minimum amount of brine
  3. customThe organic layer was dried
  4. customthe solvents evaporated
  5. customthe crude material purified by chromatography on silica gel
  6. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-ad0c1099a691405d99372083342fd252
Source dataset
uspto-grants-1987_02
Patent number
US04640913

Linked notes

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