Water → HCID 86667556, compound

HRID 85262Notes

Reaction equation

HRID 85262 reaction equation
[CH2:1]([N:5]([CH2:37][CH2:38][CH2:39][CH3:40])[C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[CH:13][C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)=[C:8]([O:19][Si:20]([C:33]([CH3:36])([CH3:35])[CH3:34])([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:7]=1)[CH2:2][CH2:3][CH3:4].C([Li])CCC.CN(C)[CH:48]=[O:49].O>O1CCCC1.C(OCC)(=O)C>[CH2:37]([N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[CH:13][C:14]2[S:15][C:16]([CH:48]=[O:49])=[CH:17][CH:18]=2)=[C:8]([O:19][Si:20]([C:33]([CH3:36])([CH3:35])[CH3:34])([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:7]=1)[CH2:38][CH2:39][CH3:40]

Participants

7

Reactant 4

HCID 962Water2×HCID 6228DimethylformamideHCID 68009142Dibutyl[3-(tert-butyldiphenylsiloxy)-4-[2-(thiophene-2-yl)vinyl]phenyl]amineHCID 178418339Butyllithium

Product 1

HCID 86667556HCID 86667556, compoundYield 81.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-71.5 °C

Procedure

In a stream of argon, in 25 ml of tetrahydrofuran was dissolved 2.32 g (4.09 mmol) of dibutyl[3-(tert-butyldiphenylsiloxy)-4-[2-(thiophene-2-yl)vinyl]phenyl]amine, and 3.8 ml of n-butyllithium (1.6 mol solution in hexane) (6.08 mmol) was added dropwise thereto under cooling at −70 to −73° C. After the mixture was stirred for 1 hour, 0.4 ml (5.77 mmol) of N,N-dimethylformamide was added dropwise. The reaction mixture was stirred for 1 hour and the temperature was allowed to rise. To this mixture, 10 ml of water was added dropwise. After the reaction mixture was poured into water, extraction with ethyl acetate, washing with a saturated saline solution, drying over anhydrous sodium sulfate, and concentration were performed. The residual liquid was dissolved in 200 ml of ether and 100 mg of iodine pieces were added thereto. After stirred at room temperature, the mixture was washed with a 5% sodium bisulfite solution and then with a saturated saline solution. Drying over anhydrous sodium sulfate and concentration were performed. The residue was purified by silica gel column chromatography to give 1.99 g of a dark red oily matter (yield: 81.9%).

Workup

  1. additionwas added dropwise
  2. stirringThe reaction mixture was stirred for 1 hour
  3. washwashing with a saturated saline solution
  4. dry with materialdrying over anhydrous sodium sulfate, and concentration
  5. dissolutionThe residual liquid was dissolved in 200 ml of ether
  6. addition100 mg of iodine pieces were added
  7. stirringAfter stirred at room temperature
  8. washthe mixture was washed with a 5% sodium bisulfite solution
  9. dry with materialDrying over anhydrous sodium sulfate and concentration
  10. customThe residue was purified by silica gel column chromatography
  11. customto give 1.99 g of a dark red oily matter (yield: 81.9%)

Sources & evidence

ORD record
ord-04f0236f8dab4dab9b0d7efbf2da8d21
Source dataset
uspto-grants-2014_09
Patent number
US08846955B2

Reaction notes

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