Tetrahydrofuran → HCID 57010306, compound

HRID 439874Notes

Reaction equation

HRID 439874 reaction equation
[CH2:1]([O:3][C:4]1[C:12]([CH3:13])=[CH:11][C:10]2[N:9]=[C:8]3[C:14]4[C:19]([CH2:20][C:7]3([CH3:21])[C:6]=2[C:5]=1[CH3:22])=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH3:2].O1CCC[CH2:24]1>C[Li].CCOCC>[CH2:1]([O:3][C:4]1[C:12]([CH3:13])=[CH:11][C:10]2[NH:9][C@:8]3([CH3:24])[C:14]4[C:19]([CH2:20][C@:7]3([CH3:21])[C:6]=2[C:5]=1[CH3:22])=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH3:2]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 22408471HCID 22408471, compound

Product 1

HCID 57010306HCID 57010306, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 178418348HCID 178418348, compoundSolvent

Procedure

To a cold (-78° C.) solution of 2.0 g (0.0063 mol) of 9b,10-dihydro-8-ethoxy-7,9,9b-trimethylindeno[1,2-b]indole in 20 ml of dry tetrahydrofuran, 10 ml of methyllithium (1.6N) in ether was added dropwise with stirring and under argon. After the addition was complete the stirring was continued for 1 hour at -20° C. and then for 1 hour at room temperature. The reaction mixture was quenched by addition of 20 ml of saturated ammonium chloride solution. After addition of 100 ml of ether the organic phase was separated and washed twice with ammonium chloride solution. Drying (Na2SO4) and evaporation gave 2.0 g (96%) of the product. 1H NMR (CDCl3): 1.35 (3H,t), 1.4 (6H,d), 2.1 (3H,s), 2.35 (3H,s), 2.95-3.05 (1H,d), 3.55-3.75 (3H,m), 6.1 (1H,s), 7.0-7.3 (4H,m).

Workup

  1. additionAfter the addition
  2. waitfor 1 hour at room temperature
  3. customThe reaction mixture was quenched by addition of 20 ml of saturated ammonium chloride solution
  4. additionAfter addition of 100 ml of ether the organic phase
  5. customwas separated
  6. washwashed twice with ammonium chloride solution
  7. customDrying
  8. custom(Na2SO4) and evaporation

Sources & evidence

ORD record
ord-6f012bff6ab64dc281ba1d049c0d9112
Source dataset
uspto-grants-1996_05
Patent number
US05516788

Reaction notes

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