Water → HCID 18706982, compound

HRID 1422082Notes

Reaction equation

HRID 1422082 reaction equation
[CH2:1]([C:3]1[C:11]2[N:6]3[C:7](=[CH:12][C:13]([CH2:14][OH:15])=[C:5]3[C:4]=1[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)[CH:8]=[CH:9][CH:10]=2)[CH3:2].[Na].S(OC)(O[CH3:29])(=O)=O.O>O1CCCC1.C(OCC)C>[CH2:1]([C:3]1[C:11]2[N:6]3[C:7](=[CH:12][C:13]([CH2:14][O:15][CH3:29])=[C:5]3[C:4]=1[C:16]1[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=1)[CH:8]=[CH:9][CH:10]=2)[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 5360545SodiumHCID 18706902HCID 18706902, compound

Product 1

HCID 18706982HCID 18706982, compoundYield 71.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-Ethyl-3-hydroxymethyl-2-(4-methoxyphenyl)pyrrolo[2,1,5-cd]indolizine (0.40 g, 1.31 mmol) was dissolved in 15 ml of dry tetrahydrofuran under a nitrogen atmosphere. Sodium hydrode (50% in oil) (0.06 g, 1.3 mmol) was added, and stirring was continued for 1/2 hour. Dimethyl sulfate (0.283 g, 2.25 mmol) was added, and the mixture was stirred at room temperature for 1day. 15 ml of water was added dropwise, and ther eaction mixture was diluted with 25 ml of diethyl ether. The organic material was extracted into diethyl ether, and the combined organic layers was washed with brine and dried over magnesium sulfate. The solvent was evaporated to afford 0.3 g (70%) of 1-ethyl-3-methoxymethyl-2-(4-methyoxyphenyl)pyrrolo[2,1,5-cd]indolizine. HPLC (Eluent: 65% CH3CN isocratic, 35% buffer H3PO4 pH=3): Rt=23.75 min (94% purity). 1H-NMR (CDCl3 /CD3OD, 200 MHz) δ: 1.42 (t, 3H); 3.16 (q, 2H); 3.41 (s, 3H); 3.88 (s, 3H); 4.78 (s, 2H); 7.07 (d, 2H); 7.21 (s, 1H); 7.56-7.69 (m, 3H); 7.81-7.91 (m, 2H).

Workup

  1. stirringthe mixture was stirred at room temperature for 1day
  2. extractionThe organic material was extracted into diethyl ether
  3. washthe combined organic layers was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-1ef2ac8645c74f80be5909feee11a453
Source dataset
uspto-grants-2000_06
Patent number
US06080754

Reaction notes

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