Water → HCID 90175305, compound

HRID 1748941Notes

Reaction equation

HRID 1748941 reaction equation
C[Si](C)(C)[C:3]1[Se:7][C:6]2=[C:8]([O:28][CH2:29][CH:30]([CH2:35][CH3:36])[CH2:31][CH2:32][CH2:33][CH3:34])[C:9]3[CH:13]=[C:12]([Si](C)(C)C)[Se:11][C:10]=3[C:18]([O:19][CH2:20][CH:21]([CH2:26][CH3:27])[CH2:22][CH2:23][CH2:24][CH3:25])=[C:5]2[CH:4]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[CH2:35]([CH:30]([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:29][O:28][C:8]1[C:6]2[Se:7][CH:3]=[CH:4][C:5]=2[C:18]([O:19][CH2:20][CH:21]([CH2:26][CH3:27])[CH2:22][CH2:23][CH2:24][CH3:25])=[C:10]2[Se:11][CH:12]=[CH:13][C:9]=12)[CH3:36]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 90174952HCID 90174952, compound

Product 1

HCID 90175305HCID 90175305, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,6-bis(trimethysilyl)-4,8-bis(2-ethylhexyloxy)benzo[1,2-b:4,5-b′]diselenophene (11) (0.29 g, 0.423 mmol) in THF (10 mL) was added 1.3 mL of tetrabutylammonium fluoride (1 M solution in THF). The resulted solution was stirred for 3 hours at room temperature water was added (40 mL) then extracted with chloroform (2×40 mL). The extract was dried over MgSO4 (anhydrous), and concentrated in vacuo. The residue was purified by column chromatography on silica gel (hexane:CH2Cl2, 98:2) to give yellow oil (0.21 g, 92%). 1H-NMR(CDCl3): δ 7.90 (d, J=5.9 Hz, 2H), 7.73 (d, J=5.9 Hz, 2H), 4.12 (d, J=5.5 Hz, 4H), 1.80 (m, 2H), 1.35-1.70 (m, 12H), 1.03 (t, J=4.9 Hz, 6H), 0.94 (t, J=4.8 Hz, 6H). MS (EI) Calculated. 540.5 found [M+1]+ 541.5.

Workup

  1. additionwas added (40 mL)
  2. extractionthen extracted with chloroform (2×40 mL)
  3. dry with materialThe extract was dried over MgSO4 (anhydrous)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (hexane:CH2Cl2, 98:2)

Sources & evidence

ORD record
ord-393843bcae524e0b893ae933b66058f7
Source dataset
uspto-grants-2015_10
Patent number
US09153785B2

Reaction notes

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