Water → HCID 20242796, compound

HRID 483135Notes

Reaction equation

HRID 483135 reaction equation
C[O:2][C:3](=[O:25])[CH2:4][C:5]1([CH2:23][CH3:24])[C:17]2[NH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][C:14]=3[CH2:18][CH3:19])[C:9]=2[CH:8]([C:20]([CH3:22])=[CH2:21])[CH2:7][CH2:6]1.C([O-])([O-])=O.[K+].[K+].O>CO>[CH3:22][C:20]([CH:8]1[C:9]2[C:10]3[C:15](=[C:14]([CH2:18][CH3:19])[CH:13]=[CH:12][CH:11]=3)[NH:16][C:17]=2[C:5]([CH2:23][CH3:24])([CH2:4][C:3]([OH:25])=[O:2])[CH2:6][CH2:7]1)=[CH2:21]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 53765558HCID 53765558, compound

Product 1

HCID 20242796HCID 20242796, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The 4-(1-methylethenyl)-1,8-diethyl-2,3,4,9-tetrahydro-1H-carbazole-1-acetic acid methyl ester (1.72 g, 5.08 mmol), prepared in Step (b), derived from the less polar ketone, and 7.11 mmol of K2CO3 (0.983 g) were refluxed under nitrogen in 40.6 ml of MeOH containing 5.1 ml of water. After 24 hours, most of the methanol was removed in vacuo and the residue was dissolved in 15 ml of water. It was acidified to pH~1 with 3M HCl (aq.) and extracted with 4×40 ml of ether. Drying (MgSO4) and flash chromatography afforded 1.51 g (4.65 mmol, 91%) of yellow oil. The compound was recrystallized from 2:1 petroleum ether/benzene to give 988 mg of white powder which was dried at 78° C. (high vacuum, phosphorous pentoxide) m.p. 133.5°-135° C.

Workup

  1. custommost of the methanol was removed in vacuo
  2. dissolutionthe residue was dissolved in 15 ml of water
  3. extractionextracted with 4×40 ml of ether
  4. dry with materialDrying (MgSO4) and flash chromatography

Sources & evidence

ORD record
ord-252dd2a34de0461db372f8ea3d54a9f9
Source dataset
uspto-grants-1986_03
Patent number
US04578398

Reaction notes

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