Lithium iodide → HCID 136029315, compound

HRID 2234744Notes

Reaction equation

HRID 2234744 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[C:22]([O:23]C)=[CH:21][C:20]4[C:19]5[C:14](=[CH:15][C:16]([C:25]6[O:26][C:27]7[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][C:28]=7[N:29]=6)=[CH:17][CH:18]=5)[C:13]([CH2:38][CH2:39][CH3:40])([CH2:35][CH2:36][CH3:37])[C:12]=4[CH:11]=3)=[N:7][C:6]=2[CH:41]=1.[I-].[Li+]>N1C(C)=CC(C)=CC=1C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[C:22]([OH:23])=[CH:21][C:20]4[C:19]5[C:14](=[CH:15][C:16]([C:25]6[O:26][C:27]7[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][C:28]=7[N:29]=6)=[CH:17][CH:18]=5)[C:13]([CH2:38][CH2:39][CH3:40])([CH2:35][CH2:36][CH3:37])[C:12]=4[CH:11]=3)=[N:7][C:6]=2[CH:41]=1

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 59297261HCID 59297261, compound

Product 1

HCID 136029315HCID 136029315, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 79532,4,6-TrimethylpyridineSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of a solution of 2,7-bis(5-methylbenzoxazol-2-yl)-9,9-dipropyl-3-methoxyfluorene] (34.6 g, 0.0638 mol) and 2,4,6-collidine (250 mL) that was prepared under argon by stirring and heating to 95° C. To this solution, dry lithium iodide (14.9 grams, 0.111 mol) was added and the resulting mixture was heated to reflux for 30 minutes and then allowed to cool to room temperature. The reaction was quenched with a mixture of concentrated HCl (167 mL), water (300 mL) and ice (500 g). The product was collected and washed with a minimum of water and methanol to afford upon drying crude product (40 g). Purification by extraction from of acidic alumina (3 cm3) on Ace-Kauffman column with methylcyclohexane gave 2,7-bis(5-methylbenzoxazol-2-yl)-9,9-dipropyl-3-hydroxyfluorene (24.93 g, yield 74%).

Workup

  1. customwas prepared under argon
  2. temperaturethe resulting mixture was heated
  3. temperatureto reflux for 30 minutes
  4. temperatureto cool to room temperature
  5. customThe reaction was quenched with a mixture of concentrated HCl (167 mL), water (300 mL) and ice (500 g)
  6. customThe product was collected
  7. washwashed with a minimum of water and methanol
  8. customto afford
  9. dry with materialupon drying crude product (40 g)
  10. customPurification
  11. extractionby extraction from of acidic alumina (3 cm3) on Ace-Kauffman column with methylcyclohexane

Sources & evidence

ORD record
ord-7a3b7455c1c54e29b7067f49be97e972
Source dataset
uspto-grants-2010_05
Patent number
US07713452B2

Reaction notes

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