1-Bromooctadecane → HCID 15704253, compound

HRID 892487Notes

Reaction equation

HRID 892487 reaction equation
[SH:1][C:2]1[S:6][C:5]([S:7][CH:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][O:11][C:10]3[CH:19]=[CH:20][C:21]([C:23]([O:25][CH3:26])=[O:24])=[CH:22][C:9]2=3)=[N:4][N:3]=1.[CH2:27](Br)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:44]([S:1][C:2]1[S:6][C:5]([S:7][CH:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][O:11][C:10]3[CH:19]=[CH:20][C:21]([C:23]([O:25][CH3:26])=[O:24])=[CH:22][C:9]2=3)=[N:4][N:3]=1)[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH3:27]

Participants

5

Reactant 3

HCID 82181-BromooctadecaneHCID 11430Potassium CarbonateHCID 178497122HCID 178497122, compound

Product 1

HCID 15704253HCID 15704253, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

After 50 ml of an N,N-dimethylformamide solution containing a mixture of 2.0 g of Compound 153a obtained in Example 119, 2 ml of octadecyl bromide and 2.0 g of potassium carbonate was stirred at 80° C. at 1.5 hours, the solvent was distilled off under reduced pressure. The aqueous phase was extracted with 200 ml of methylene chloride. The extract was washed with saturated sodium chloride aqueous solution. After drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluting solvent; hexane:ethyl acetate=15:1) to give 0.8 g of the product.

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. extractionThe aqueous phase was extracted with 200 ml of methylene chloride
  3. washThe extract was washed with saturated sodium chloride aqueous solution
  4. dry with materialAfter drying over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. washThe resulting residue was subjected to silica gel column chromatography (eluting solvent; hexane:ethyl acetate=15:1)

Sources & evidence

ORD record
ord-4d18bc25988943eb8f61c219591ee356
Source dataset
uspto-grants-1992_06
Patent number
US05118701

Reaction notes

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