Hexane → HCID 131724427, compound

HRID 1581737Notes

Reaction equation

HRID 1581737 reaction equation
[Li][CH2:2][CH2:3][CH2:4][CH3:5].CCCCCC.C([N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]2[C:23]3[C:28](CC1=2)=[CH:27][CH:26]=[CH:25][CH:24]=3)C.[C:30]([NH:34][Si:35]([CH3:38])([CH3:37])Cl)([CH3:33])([CH3:32])[CH3:31]>CCOCC>[CH3:37][SiH:35]([N:34]([CH2:2][CH2:3][CH:4]1[C:5]2[NH:14][C:22]3[C:17]([C:16]=2[C:23]2[C:24]1=[CH:25][CH:26]=[CH:27][CH:28]=2)=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:30]([CH3:33])([CH3:32])[CH3:31])[CH3:38]

Participants

6

Reactant 4

HCID 8058HexaneHCID 11205972t-ButylaminodimethylsilylchlorideHCID 22722354HCID 22722354, compoundHCID 178418339Butyllithium

Product 1

HCID 131724427HCID 131724427, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

8.02 mL of n-BuLi 2.5 M in hexane (20.04 mmol) were added dropwise at 0° C. to a solution of 4.30 g of N-ethyl-5,6-dihydroindeno[2,1-b]indole (Mw=233.31, purity 98.9%, 18.22 mmol) in Et2O. At the end of the addition, the reaction mixture was allowed to warm up to room temperature and stirred for two hours. The dark brown solution obtained was added at 0° C. to a solution of 4.32 g of (tert-butylamino)dimethylchlorosilane (Mw=165.74, purity 83.7% wt., d=0.887, 21.86 mmol) in Et2O. The final mixture was allowed to warm up to room temperature and stirred for three hours. Then the solvents were evaporated under reduced pressure to give a residue (8.73 g) which was extracted with 50 mL of toluene. The extract, a sticky brown solid (7.48 g), was washed with pentane obtaining 4.32 g of a light brown powder, which was analyzed by 1H-NMR. The 1H-NMR analysis showed a purity of 96.6% wt. in the desired ligand together with a 3.4% wt. of starting N-ethyl-5,6-dihydroindeno[2,1-b]indole. Yield=63.1%.

Workup

  1. additionAt the end of the addition
  2. customThe dark brown solution obtained
  3. temperatureto warm up to room temperature
  4. stirringstirred for three hours
  5. customThen the solvents were evaporated under reduced pressure

Sources & evidence

ORD record
ord-d486231b41a041ada32972442e51640d
Source dataset
uspto-grants-2004_05
Patent number
US06730754B2

Reaction notes

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