Tetrahydrofuran → HCID 21954381, compound

HRID 661813Notes

Reaction equation

HRID 661813 reaction equation
[CH:1]1[C:13]2[N:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]4[CH:25]=[CH:24][C:23]([N:26]5[C:38]6[CH:37]=[CH:36][C:35]([CH:39]=[O:40])=[CH:34][C:33]=6[C:32]6[C:27]5=[CH:28][CH:29]=[CH:30][CH:31]=6)=[CH:22][CH:21]=4)=[CH:16][CH:15]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.O1CCCC1.[BH4-].[Na+]>CO>[CH:1]1[C:13]2[N:12]([C:14]3[CH:15]=[CH:16][C:17]([C:20]4[CH:21]=[CH:22][C:23]([N:26]5[C:38]6[CH:37]=[CH:36][C:35]([CH2:39][OH:40])=[CH:34][C:33]=6[C:32]6[C:27]5=[CH:28][CH:29]=[CH:30][CH:31]=6)=[CH:24][CH:25]=4)=[CH:18][CH:19]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 21954379HCID 21954379, compound

Product 1

HCID 21954381HCID 21954381, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 100-ml Kolben equipped with a stirrer and a condenser was charged under a nitrogen stream with 18 g (15.6 mmol) of 4-(carbazol-9-yl)-4′-(3-formylcarbazol-9-yl)-biphenyl prepared above and 800 ml of tetrahydrofuran. Sodium tetrahydroborate (0.65 g, 17.2 mmol) was introduced at room temperature into the above mixture, and the mixture was stirred for one hr. Thereafter, 160 ml of methanol was introduced into the reaction solution, and the mixture was stirred for 3 hr. The solvent was distilled off, and the residue was dissolved in 500 ml of toluene. The solution was washed with water, and the solvent was then distilled off to give 4-(carbazol-9-yl)-4′-(3-hydroxymethylcarbazol-9-yl)-biphenyl (7.9 g, yield 98.4%).

Workup

  1. customA 100-ml Kolben equipped with a stirrer and a condenser
  2. stirringthe mixture was stirred for 3 hr
  3. distillationThe solvent was distilled off
  4. dissolutionthe residue was dissolved in 500 ml of toluene
  5. washThe solution was washed with water
  6. distillationthe solvent was then distilled off

Sources & evidence

ORD record
ord-956d6ac7e4654ff7bf284595cdfd8f86
Source dataset
uspto-grants-2011_12
Patent number
US08084935B2

Reaction notes

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