N-bromobutanimide → HCID 53938208, compound

HRID 37609Notes

Reaction equation

HRID 37609 reaction equation
[C:1]1([CH:7]=[CH:8][C:9]([O:16][Si](C)(C)C)=[CH:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:21]N1C(=O)CCC1=O>O1CCCC1>[Br:21][CH:10]([C:9](=[O:16])[CH:8]=[CH:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:11][C:12]([O:14][CH3:15])=[O:13]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 53778801Methyl 6-phenyl-4-[(trimethylsilyl)-oxy]-hexa-3,5-dienoate

Product 1

HCID 53938208HCID 53938208, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 4.2 g of the product of Step C, 40 ml of tetrahydrofuran and 2.7 g of N-bromo-succinimide was cooled to 0° C. and stirred for one hour at this temperature, then brought to dryness. The residue was chromatographed on silica, eluting with a hexane--ethyl acetate mixture (8-2) to obtain 1.9 g of the expected product. Thin layer chromatography; Rf=0.28 [eluant: hexane-- ethyl acetate (8-2)].

Workup

  1. customThe residue was chromatographed on silica
  2. washeluting with a hexane

Sources & evidence

ORD record
ord-af4eef035c10466a9d154e4da6b4f2b9
Source dataset
uspto-grants-1995_05
Patent number
US05420340

Reaction notes

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