Triethylamine → HCID 57429591, compound

HRID 605486Notes

Reaction equation

HRID 605486 reaction equation
[CH2:1]([O:5][C:6]([C:8]1([C:11](=[O:13])[CH3:12])[CH2:10][CH2:9]1)=[O:7])[CH2:2][CH2:3][CH3:4].C(N(CC)CC)C.FC(F)(F)S(O[Si](CC)(CC)CC)(=O)=O.[Br:36]N1C(=O)CCC1=O>C(Cl)Cl>[CH2:1]([O:5][C:6]([C:8]1([C:11](=[O:13])[CH2:12][Br:36])[CH2:9][CH2:10]1)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 67184N-bromobutanimideHCID 2733308Triethylsilyl trifluoromethanesulphonateHCID 57429590HCID 57429590, compound

Product 1

HCID 57429591HCID 57429591, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 15 (3.30 g, 17.9 mmol) in methylene chloride (150 mL) and triethylamine (5.01 mL, 3.61 g, 35.7 mmol), was added dropwise triethylsilyl trifluoromethanesulphonate (4.07 mL, 4.72 g 17.9 mmol) at 0° C. After 20 minutes, N-bromosuccinimide (3.53 g, 19.8 mmol) was added, and the cooling bath was removed. Water (50 mL) was then added, and the mixture was extracted with methylene chloride (3×100 mL). The organic phase was dried over anhydrous MgSO4, concentrated under reduced pressure, and the residue was purified by column chromatography (3-10% ethyl acetate/hexane) to give 3.42 g (13.0 mmol; 73% yield) of 16. 1H NMR MHz, CDCl3) δ 0.96 (3H, t, J=7.4 Hz), 1.47 (2H, m), 1.60-1.66 (6H, m), 4.16 (2H, t, J=6.7 Hz), 4.50 (2H, s). 13C NMR (100 MHz, CDCl3) δ 13.7, 19.2, 21.2, 30.5, 33.2, 35.1, 65.5, 170.4, 197.6. MS (EI) m/z 264 (40, M+), 262 (39, M+), 208 (20), 206 (20), 190 (56), 188 (54), 183 (71), 169 (100); exact mass (ESI) calculated for C10H15O3BrNa ([M+Na]+) 285.0102, found 285.0114.

Workup

  1. customthe cooling bath was removed
  2. additionWater (50 mL) was then added
  3. extractionthe mixture was extracted with methylene chloride (3×100 mL)
  4. dry with materialThe organic phase was dried over anhydrous MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customthe residue was purified by column chromatography (3-10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f6b7b44185fa4cfda7932de00d0ae610
Source dataset
uspto-grants-2011_03
Patent number
US07915242B2

Reaction notes

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