Tetrabutylammonium Fluoride → HCID 57675743, compound

HRID 2264700Notes

Reaction equation

HRID 2264700 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[C:16]2[CH2:24][CH2:25][O:26][Si](C(C)(C)C)(C)C)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[C:16]2[CH2:24][CH2:25][OH:26])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57675759HCID 57675759, compound

Product 1

HCID 57675743HCID 57675743, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(4-Benzyloxyphenyl)-2-[2-(tert-butyldimethylsilanyloxy)ethyl]-1H-indole (0.62 mmol, 1.35 mmol) was dissolved in tetrahydrofuran (6 mL) under N2, and tetrabutylammonium fluoride (1.49 mL, 1 M in tetrahydrofuran, 1.49 mmol) was added. The reaction was stirred for 2 hours, then quenched with saturated ammonium acetate. The mixture was extrated with ethyl acetate, dried over MgSO4, and concentrated. The residue was passed through a plug of silica with ethyl acetate. The filtrate was concentrated to give the desired product. The reaction was assumed to be quantitative. LC-MS (C23H21NO2 calc'd 343) m/z 344 (M+H).

Workup

  1. customquenched with saturated ammonium acetate
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-38bc4fcbf8324f3da2af29bd9f670354
Source dataset
uspto-grants-2010_12
Patent number
US07855224B2

Reaction notes

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