Tetrabutylammonium Fluoride → HCID 59153336, compound

HRID 601939Notes

Reaction equation

HRID 601939 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH:19](=[C:26]1/[C:27]2[CH:28]=[C:29]([C:43]([O:45][CH3:46])=[O:44])[N:30](COCC[Si](C)(C)C)[C:31]=2[CH2:32][CH2:33][CH2:34]/1)\[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1>[CH:19](=[C:26]1/[C:27]2[CH:28]=[C:29]([C:43]([O:45][CH3:46])=[O:44])[NH:30][C:31]=2[CH2:32][CH2:33][CH2:34]/1)\[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59153332HCID 59153332, compound

Product 1

HCID 59153336HCID 59153336, compoundYield 13.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

Tetrabutylammonium fluoride (TBAF) (23 mL, 1M in THF, 23 mmol) was added over 5 min to a solution of (E)-methyl 4-benzylidene-1-((2-(trimethylsilyl)ethoxy)methyl)-4,5,6,7-tetrahydro-1H-indole-2-carboxylate (900 mg, 2.26 mmol) in cooled THF (0° C.). The reaction mixture was then heated for 4 h at 80° C. After 48 h at rt, the reaction mixture was partitioned between ether and water. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by silica gel chromatography (cyclohexane/EtOAc:80/20) to afford the (E)-methyl 4-benzylidene-4,5,6,7-tetrahydro-1H-indole-2-carboxylate (80 mg). LC/MS: 76%, m/z=267.

Workup

  1. customthe reaction mixture was partitioned between ether and water
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by silica gel chromatography (cyclohexane/EtOAc:80/20)

Sources & evidence

ORD record
ord-86eea4db8425447eb464c9480fd55cda
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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