Sodium Hydroxide → HCID 86629954, compound

HRID 1908945Notes

Reaction equation

HRID 1908945 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.[OH-].[Na+].[C:17]([O:21][C:22](=O)[O:23]C(C)(C)C)([CH3:20])([CH3:19])[CH3:18]>C1(C)C=CC=CC=1.O.[Cl-].C([N+](CCCC)(CCCC)CC1C=CC=CC=1)CCC>[C:22]([N:6]1[C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:14][C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2)([O:21][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:23]

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 207463-MethylcarbazoleHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 86629954HCID 86629954, compoundYield 96%

Reagents, catalysts & solvents 3

HCID 159952Benzyltributylammonium chlorideCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-methylcarbazole (500 mg, 2.76 mmol) in toluene (7.5 mL), was added sodium hydroxide (5 g, 125 mmol) as a solution in water (15 mL) followed by tri n-butyl benzyl ammonium chloride (25 mg). The two-phase solution was stirred at about 0° C. and di t-butylcarbonate (1.25 g, 5.7 mmol) was added in one portion. The mixture was stirred for about 1 h at about 0° C., the toluene layer was separated and the aqueous layer was extracted with ethyl acetate (2×10 mL). The combined organic layers were washed with water (2×10 mL); dried (MgSO4) and concentrated under in vacuo to afford the crude product (725 mg, 96% yield). ES-MS (M+H)+ 282.0 (calc. 282.1).

Workup

  1. stirringThe mixture was stirred for about 1 h at about 0° C.
  2. customthe toluene layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate (2×10 mL)
  4. washThe combined organic layers were washed with water (2×10 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under in vacuo

Sources & evidence

ORD record
ord-077b790809ab4986b1a827400e9cff2c
Source dataset
uspto-grants-2013_12
Patent number
US08598312B2

Reaction notes

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