Triethyl phosphite → 11,11-Dimethyl-5,11-dihydroindeno[1,2-b]carbazole

HRID 576457Notes

Reaction equation

HRID 576457 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:22]=[CH:21][C:20]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([CH3:24])([CH3:23])[C:12]=2[CH:11]=1)([O-])=O.P(OCC)(OCC)OCC>>[CH3:23][C:13]1([CH3:24])[C:12]2[CH:11]=[C:10]3[C:5]4[C:4]([NH:1][C:22]3=[CH:21][C:20]=2[C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]1=2)=[CH:9][CH:8]=[CH:7][CH:6]=4

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 580591942-(2-Nitrophenyl)-9,9-dimethyl-9H-fluorene

Product 1

HCID 5805920311,11-Dimethyl-5,11-dihydroindeno[1,2-b]carbazole

Procedure

A mixture of 75 g (238 mmol) of 2-(2-nitrophenyl)-9,9-dimethyl-9H-fluorene and 290.3 ml (1669 mmol) of triethyl phosphite is heated under reflux for 12 h. The triethyl phosphite which remains is subsequently removed by distillation (72-76° C./9 mm Hg). Water/MeOH (1:1) is added to the residue, and the solid is filtered off and recrystallised. Yield: 61.3 g (216 mmol), 92%.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 12 h
  3. customThe triethyl phosphite which remains is subsequently removed by distillation (72-76° C./9 mm Hg)
  4. additionWater/MeOH (1:1) is added to the residue
  5. filtrationthe solid is filtered off
  6. customrecrystallised

Sources & evidence

ORD record
ord-bc6b6943d8c3401e8afdf11933dcf891
Source dataset
uspto-grants-2015_05
Patent number
US09040172B2

Reaction notes

Loading…