18-Crown-6 → HCID 21270674, compound

HRID 1193865Notes

Reaction equation

HRID 1193865 reaction equation
CC(C)([O-])C.[K+].C1OCCOCCOCCOCCOCCOC1.[CH2:25]([O:27][C:28]1[CH:36]=[C:35]2[C:31]([CH:32]=[CH:33][NH:34]2)=[CH:30][CH:29]=1)[CH3:26].Br[CH2:38][C:39]([O:41][CH3:42])=[O:40]>CCOCC.O>[CH3:42][O:41][C:39](=[O:40])[CH2:38][N:34]1[C:35]2[C:31](=[CH:30][CH:29]=[C:28]([O:27][CH2:25][CH3:26])[CH:36]=2)[CH:32]=[CH:33]1

Participants

7

Reactant 4

HCID 2855718-Crown-6HCID 60984Methyl bromoacetateHCID 5267696-Ethoxy-1H-indoleHCID 23665647Potassium tert-butoxide

Product 1

HCID 21270674HCID 21270674, compoundYield 96.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

Potassium tert-butoxide (0.77 g, 6.9 mmol) was stirred with dry ether (50 ml) containing 18-crown-6 (0.164 g, 0.62 mmol). 6-Ethoxyindole (1.0 g, 6.2 mmol) was added portionwise over 15 minutes at room temperature. This was stirred for 1/2 hour then cooled to 0° C. when methyl bromoacetate (0.65 ml, 6.9 mmol) in ether (5 ml) was added dropwise. The reaction mixture was stirred for 16 hours at room temperature then poured into water (150 ml) and extracted with ether (2×100 ml). The extracts were washed with brine (2×75 ml), dried and concentrated to give crude methyl(6-ethoxyindol-1-yl)acetate (1.4 g, 96% yield) as a brown oil.

Workup

  1. additionwas added dropwise
  2. stirringThe reaction mixture was stirred for 16 hours at room temperature
  3. extractionextracted with ether (2×100 ml)
  4. washThe extracts were washed with brine (2×75 ml)
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-172ace2f656345ccb395d23833fb26da
Source dataset
uspto-grants-1989_03
Patent number
US04812162

Reaction notes

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