1-Bromooctadecane → HCID 4178220, compound

HRID 1608028Notes

Reaction equation

HRID 1608028 reaction equation
[OH:1][CH2:2][C:3]1([CH2:8][OH:9])[CH2:7][CH2:6][CH2:5][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>[OH:1][CH2:2][C:3]1([CH2:8][O:9][C:30]([NH:31][CH2:10][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])[CH2:7][CH2:6][CH2:5][O:4]1

Participants

7

Reactant 3

HCID 82181-BromooctadecaneHCID 263157tetrahydrofuran-2,2-diyldimethanolHCID 11378442Potassium cyanate

Product 1

HCID 4178220HCID 4178220, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 2.64 g (20 mmol) of 2,2-bis(hydroxymethyl)tetrahydrofuran, 7.99 g (24 mmol) of octadecyl bromide, 2.43 g (30 mmol) of potassium cyanate and 0.644 g (2 mmol) of tetrabutyl ammonium bromide in 300 ml of dry acetonitrile was refluxed, with stirring, at 100° C. for 23 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 a mixture of petroleum ether and ethyl acetate in a 4:1 ratio as the eluent to yield the title compound as a solid, m.p. 57°-58° 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
  5. additiona mixture of petroleum ether and ethyl acetate in a 4:1 ratio as the eluent

Sources & evidence

ORD record
ord-2d79c01ab5624e9ab5994af626af5d9a
Source dataset
uspto-grants-1989_09
Patent number
US04868319

Reaction notes

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