Lithium hydroxide, monohydrate → HCID 43509865, compound

HRID 1965917Notes

Reaction equation

HRID 1965917 reaction equation
C([O:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[C:21]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2)(=O)C.O.[OH-].[Li+]>C1COCC1>[CH:11]1[C:10]2[N:9]([CH2:8][CH2:7][CH2:6][CH2:5][OH:4])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]=2[CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68423402HCID 68423402, compound

Product 1

HCID 43509865HCID 43509865, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

Compound 9 (35.1 g, 0.125 mol) and lithium hydroxide monohydrate (13.0 g, 0.31 mol) were dissolved in 200 mL THF. The reaction mixture was stirred at 80° C. for 12 hours. The mixture was filtered and the homogeneous solution was evaporated to give the crude product. The resulting product was purified by silica gel column chromatography (eluent: ethyl acetate:methylene chloride=1:10 v/v) to yield 26 g (86%) of 4-(9H-carbazol-9-yl)butan-1-ol (Compound 10).

Workup

  1. filtrationThe mixture was filtered
  2. customthe homogeneous solution was evaporated
  3. customto give the crude product
  4. customThe resulting product was purified by silica gel column chromatography (eluent: ethyl acetate:methylene chloride=1:10 v/v)

Sources & evidence

ORD record
ord-6fd2c971d9a14cfeb470c62c0a7c864f
Source dataset
uspto-grants-2013_04
Patent number
US08420231B2

Reaction notes

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