Water → HCID 71254179, compound

HRID 332115Notes

Reaction equation

HRID 332115 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[NH:7][C:8]3[C:13]([C:14]=2[CH:15]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3)#[N:2].[Li]CCCC.[O:21]1[CH:23]([CH2:24][O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:22]1.O>C1COCC1>[OH:21][CH:23]([CH2:24][O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:22][N:7]1[C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:15][C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2

Participants

6

Reactant 4

HCID 962WaterHCID 31217Phenyl glycidyl etherHCID 21107343HCID 21107343, compoundHCID 178418339Butyllithium

Product 1

HCID 71254179HCID 71254179, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 3-cyano-9H-carbazole (0.4998 g, 2.6 mmol, 1 equiv) in THF (40 mL) was added nBuLi (1.6 M in hexane, 3.25 mL, 5.2 mmol, 2 equiv). The mixture was stirred at −78° C. for 2 hours. 1,2-epoxy-3-phenoxypropane (0.7809 g, 5.2 mmol, 2 equiv) was added and the mixture was stirred at 45° C. overnight. Water (50 mL) was added and the mixture was extracted by dichloromethane (3×30 mL). The combined dichloromethane layers were washed by brine (2×30 mL) and then dried over Na2SO4. The solvent was removed under reduced pressure, and the product was chromatographed on silica gel with dichloromethane to yield 0.7736 g white foamed solid (86%).

Workup

  1. stirringthe mixture was stirred at 45° C. overnight
  2. extractionthe mixture was extracted by dichloromethane (3×30 mL)
  3. washThe combined dichloromethane layers were washed by brine (2×30 mL)
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed under reduced pressure
  6. customthe product was chromatographed on silica gel with dichloromethane
  7. customto yield 0.7736 g

Sources & evidence

ORD record
ord-b349fcaa795f431e9ece1386572dd509
Source dataset
uspto-grants-2014_11
Patent number
US08877797B2

Reaction notes

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