1-Bromooctadecane → HCID 14670276, compound

HRID 1608027Notes

Reaction equation

HRID 1608027 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:7][CH2:6][C@@H:5]([CH2:8][OH:9])[O:4]1.[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][CH2:25][CH2:26][CH3:27].[O-:29][C:30]#[N:31].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C.C(Cl)Cl>[CH2:10]([NH:31][C:30]([O:1][CH2:2][C@H:3]1[CH2:7][CH2:6][C@@H:5]([CH2:8][OH:9])[O:4]1)=[O:29])[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][CH2:25][CH2:26][CH3:27]

Participants

7

Reactant 3

HCID 82181-BromooctadecaneHCID 11378442Potassium cyanateHCID 12886254cis-2,5-Bis(hydroxymethyl)tetrahydrofuran

Product 1

HCID 14670276HCID 14670276, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 2.64 g (20 mmol) of cis-2,5-bis(hydroxymethyl)tetrahydrofuran, 7.99 g (24 mmol) of octadecyl bromide, 2.43 g (30 mmol) of potassium cyanate and 0.966 g (3 mmol) of tetrabutyl ammonium bromide in 100 ml of dry acetonitrile was refluxed, with stirring, at 100° C. for 20 hours. The resultant mixture was then diluted with hot methylene chloride, filtered and the filtrate concentrated in vacuo. The crude product was then purified by flash silica gel chromatography employing successive mixtures of petroleum ether and ethyl acetate in ratios of 4:1, 2.33:1 and 1:1 as the eluent to yield the title compound as a solid, m.p. 79°-80° C.

Workup

  1. temperaturewas refluxed
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe crude product was then purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-dba662a89f6649d7954d82a3a1aef992
Source dataset
uspto-grants-1989_09
Patent number
US04868319

Reaction notes

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