Diethyl Ether → HCID 89463982, compound

HRID 2208632Notes

Reaction equation

HRID 2208632 reaction equation
Cl([O-])(=O)(=O)=O.[CH3:6][C:7]1([CH3:27])[C:15]2[C:14]3[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=3[CH:12]=[CH:11][C:10]=2[N+:9]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:8]1[CH3:26].C(OCC)C.[OH-].[K+]>C1C=CC=CC=1.O>[CH3:6][C:7]1([CH3:27])[C:15]2[C:14]3[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=3[CH:12]=[CH:11][C:10]=2[N:9]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:8]1=[CH2:26]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 14797Potassium HydroxideHCID 131733189HCID 131733189, compound

Product 1

HCID 89463982HCID 89463982, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

1,1,2-Trimethyl-3-phenyl-1H-benzo[e]indolium perchlorate (11) (0.386 g) was suspended in 50 ml of benzene or diethyl ether and a solution 0.1 g potassium hydroxide in 2 ml water was added. The mixture was stirred at room temperature under nitrogen for one hour. The organic solvent layer was separated and washed with water and filtered through silica gel and then dried and evaporated. The resultant oily product (0.2 g) was sufficiently pure for the next synthetic step. 1H NMR (400 MHz, DMSO) δ 8.05 (d, 1H, J=8.5), 7.81 (d, 1H, J=8.1), 7.67 (d, 1H, J=8.8), 7.59 (t, 2H, J=7.8), 7.43 (dt, 4H, J=6.9, 20.3), 7.22 (t, 1H, J=7.3), 6.75 (d, 1H, J=8.7), 4.05 (d, 1H, J=1.7), 3.88 (d, 1H, J=1.7), 1.71 (s, 6H).

Workup

  1. customThe organic solvent layer was separated
  2. washwashed with water
  3. filtrationfiltered through silica gel
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-dff7a7488e564d8ea17e4a745fb25468
Source dataset
uspto-grants-2016_06
Patent number
US09376568B2

Reaction notes

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