Potassium Carbonate → HCID 59161013, compound

HRID 1873575Notes

Reaction equation

HRID 1873575 reaction equation
[Si:1]([O:18][CH2:19][CH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26]([O:29][CH2:30][CH2:31][CH2:32]Br)(=[O:28])[CH3:27].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:26]([O:29][CH2:30][CH2:31][CH2:32][N:23]1[CH2:24][CH2:25][CH:20]([CH2:19][O:18][Si:1]([C:14]([CH3:17])([CH3:15])[CH3:16])([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:21][CH2:22]1)(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 122357751-Propanol, 3-bromo-, 1-acetateHCID 68701920HCID 68701920, compound

Product 1

HCID 59161013HCID 59161013, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5.00 g (12.44 mmol) of the compound from Example 20A are dissolved in 57 ml of acetonitrile, and 4.51 g (24.89 mmol) of 3-bromopropyl acetate and 3.44 g (24.89 mmol) of potassium carbonate are added. The reaction mixture is stirred at +80° C. for 8 h. After filtration, the solvent is removed on a rotary evaporator. The residue is taken up in 50 ml of ethyl acetate and washed in each case once with 10 ml of water and 10 ml of saturated aqueous sodium bicarbonate solution. The organic phase is dried over magnesium sulfate and the solvent is removed on a rotary evaporator. The crude product is used in the next reaction without further purification.

Workup

  1. filtrationAfter filtration
  2. customthe solvent is removed on a rotary evaporator
  3. washwashed in each case once with 10 ml of water and 10 ml of saturated aqueous sodium bicarbonate solution
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. customthe solvent is removed on a rotary evaporator
  6. customThe crude product is used in the next reaction without further purification

Sources & evidence

ORD record
ord-009e500d236e4c57b87baa4f0dc94d92
Source dataset
uspto-grants-2012_11
Patent number
US08304412B2

Reaction notes

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