Dimethylformamide → HCID 131724398, compound

HRID 2084694Notes

Reaction equation

HRID 2084694 reaction equation
[C:1]([SiH2:5][O:6][C:7]([CH3:31])([CH3:30])[CH:8]1[O:13][C:12]2=[CH:14][S:15][C:16]([CH:17]=[CH:18][C:19]3[CH:24]=[CH:23][C:22]([N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])=[CH:21][CH:20]=3)=[C:11]2[O:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[Li]CCCC.CN(C)[CH:39]=[O:40]>O1CCCC1>[C:1]([SiH2:5][O:6][C:7]([CH3:30])([CH3:31])[CH:8]1[CH2:9][O:10][C:11]2=[C:16]([CH:17]=[CH:18][C:19]3[CH:20]=[CH:21][C:22]([N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])=[CH:23][CH:24]=3)[S:15][C:14]([CH:39]=[O:40])=[C:12]2[O:13]1)([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 131724399HCID 131724399, compoundHCID 178418339Butyllithium

Product 1

HCID 131724398HCID 131724398, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

60 mL of dry tetrahydrofuran is added via syringe to 3.4 g (0.0074 mole) of 4 contained in a nitrogen purged round bottom flask. The solution is cooled to 0° C. The solution is stirred at 0° C. for 60 minutes, at which point 3.2 mL of 2.5 M BuLi in hexanes is added dropwise. The solution is allowed to stir for 15 min at 0° C., followed by the addition of 0.697 mL (0.009 mole) of anydrous dimethylformamide. The solution is warmed to room temperature, where it was stirred overnight. The tetrahydrofuran is removed under reduced pressure, and the resulting material is taken up in 500 mL of chloroform. The organic layer is washed with water three times, dried over MgSO4, and solvent is then removed under reduced pressure. The compound is purified on a silica column with a hexane/ethyl acetate mobile phase.

Workup

  1. customcontained in a nitrogen purged round bottom flask
  2. additionis added dropwise
  3. stirringto stir for 15 min at 0° C.
  4. temperatureThe solution is warmed to room temperature
  5. stirringwhere it was stirred overnight
  6. customThe tetrahydrofuran is removed under reduced pressure
  7. washThe organic layer is washed with water three times
  8. dry with materialdried over MgSO4, and solvent
  9. customis then removed under reduced pressure
  10. customThe compound is purified on a silica column with a hexane/ethyl acetate mobile phase

Sources & evidence

ORD record
ord-2a2bdbdbe3674631b0e34a315e101337
Source dataset
uspto-grants-2004_04
Patent number
US06716995B2

Reaction notes

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