Water → HCID 18437785, compound

HRID 457351Notes

Reaction equation

HRID 457351 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH2:9]([N:13]1[C:17]([CH2:18][OH:19])=[CH:16][N:15]=[C:14]1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:10][CH2:11][CH3:12].O>C(#N)C>[CH2:9]([N:13]1[C:17]([CH2:18][OH:19])=[C:16]([Br:1])[N:15]=[C:14]1[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 22493824HCID 22493824, compound

Product 1

HCID 18437785HCID 18437785, compoundYield 50.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

N-bromo succinimide (3.56 g, 20 mmol) is added to a solution of alcohol 139 (4.60 g, 20 mmol) in 100 ml of anhydrous acetonitrile cooled to 0° C., in portions over 15 minutes. The resulting mixture is stirred at 0° C. for 60 min, water is added to quench the reaction, the acetonitrile is evaporated, and the residue dissolved in 100 ml of ethyl acetate, washed with water and brine, and dried over Na2SO4 The solvent is evaporated and the residue purified by silica gel flash chromatography (hexanes/ethyl acetate, from 6:1 to 3:1) to give 3.15 g of product 140. 1H NMR (300 MHz, CDCl3) δ 7.48–7.56 (2H, m), 7.40–7.47 (3H, m), 4.67 (2H, s), 4.07 (2H, t, J=7.60 Hz), 1.65 (2H, m), 1.24 (2H, m), 0.83 (3H, t, J=7.5 Hz). MS (+VE) m/z 309 (M+), 311 (M+2).

Workup

  1. customto quench
  2. customthe reaction
  3. customthe acetonitrile is evaporated
  4. dissolutionthe residue dissolved in 100 ml of ethyl acetate
  5. washwashed with water and brine
  6. dry with materialdried over Na2SO4 The solvent
  7. customis evaporated
  8. customthe residue purified by silica gel flash chromatography (hexanes/ethyl acetate, from 6:1 to 3:1)

Sources & evidence

ORD record
ord-c31d4622764144149010be6f7a938fa6
Source dataset
uspto-grants-2007_03
Patent number
US07186734B2

Reaction notes

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