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Ethyl Acetate → HCID 19787989, compound

HRID 1656374
Notes
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Reaction equation

HRID 1656374 reaction equation
[C:1]([C:9]1[N:10]=[CH:11][C:12]2[NH:13][C:14]3[C:19]([C:20]=2[C:21]=1[CH2:22][O:23][CH3:24])=[CH:18][C:17]([O:25][Si](C(C)C)(C(C)C)C(C)C)=[CH:16][CH:15]=3)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>O1CCCC1>[C:1]([C:9]1[N:10]=[CH:11][C:12]2[NH:13][C:14]3[C:19]([C:20]=2[C:21]=1[CH2:22][O:23][CH3:24])=[CH:18][C:17]([OH:25])=[CH:16][CH:15]=3)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 19787979HCID 19787979, compound

Product 1

HCID 19787989HCID 19787989, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

530 mg of 3-benzoyl-6-triisopropylsilyloxy-4-methoxymethyl-beta-carboline was dissolved in 7.5 ml of absolute tetrahydrofuran and stirred for 0.5 hour under argon at room temperature after adding 1.1 ml of a 1.1 molar tetrabutylammonium fluoride solution in tetrahydrofuran. After adding ethyl acetate, the organic phase was washed with saturated common salt solution, dried and concentrated by evaporation. 315 mg of the title compound was obtained after absorptive precipitation with ethyl acetate/petroleum ether, melting point 258° C.

Workup

  1. washthe organic phase was washed with saturated common salt solution
  2. customdried
  3. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-34e8cec0f0c742ed89668926586e62f9
Source dataset
uspto-grants-1993_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05254563

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes