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Trimethyl orthoformate → 7-Ethyl-alpha-(phenylmethyl)-1H-indole-3-acetic Acid Methyl Ester

HRID 652367
Notes
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Reaction equation

HRID 652367 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][CH:9]=[C:8]2[CH2:12][C:13](=O)[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17]C=1)[CH3:2].[CH3:22][O:23][CH:24](OC)[O:25]C.O.O.O.[N+]([O-])([O-])=O.[Tl+3].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[Tl+]>CCOCC.CO>[CH3:22][O:23][C:24](=[O:25])[CH:12]([CH2:13][C:14]1[CH:15]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:8]1[C:7]2[C:11](=[C:3]([CH2:1][CH3:2])[CH:4]=[CH:5][CH:6]=2)[NH:10][CH:9]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 9005Trimethyl orthoformateHCID 24937Thallous nitrateHCID 11270721Nitric acid,thallium(3+) salt, trihydrate (9CI)HCID 569785881-(7-ethyl-1H-indol-3-yl)-3-phenylpropanone

Product 1

HCID 142014387-Ethyl-alpha-(phenylmethyl)-1H-indole-3-acetic Acid Methyl Ester

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent
HCID 3283Diethyl EtherSolvent

Procedure

According to the procedure of E. C. Taylor et al, J. Amer. Chem. Soc., 98, 3037 (1976), a solution of 1-(7-ethyl-1H-indol-3-yl)-3-phenylpropanone (2.77 g, 10 mmol) in a 1:1 mixture of methanol and trimethylorthoformate (25 mL) was added to thallium (III) nitrate trihydrate (4.88 g, 11 mmol), and the mixture was heated under reflux until precipitation of thallium (I) nitrate was complete (about 3 hours). The dark brown mixture was diluted with 25 mL of ether, and the thallium (I) nitrate was removed by filtration. The filtrate was washed successively with 1×50 mL portions of water, 5% aqueous sodium bicarbonate, and water and was then dried over anhydrous MgSO4. Concentration of the filtrate and flash chromatography of the crude product (20% ethyl acetate/hexane, silica gel) have the ester as a red-brown oil (0.98 g, 31.9%).

Workup

  1. temperaturethe mixture was heated
  2. custom(about 3 hours)
  3. customthe thallium (I) nitrate was removed by filtration
  4. washThe filtrate was washed successively with 1×50 mL portions of water, 5% aqueous sodium bicarbonate, and water
  5. dry with materialwas then dried over anhydrous MgSO4

Sources & evidence

ORD record
ord-9f7d841405854dca903f6b9cae27acd1
Source dataset
uspto-grants-1987_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04670462

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes