Tetrabutylammonium Fluoride → HCID 86623921, compound

HRID 1666509Notes

Reaction equation

HRID 1666509 reaction equation
C[Si](C)(C)[C:3]#[C:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][C:16]2[CH:17]=[C:18]([CH:33]=[CH:34][CH:35]=2)[CH:19]=[C:20]2[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]2)=[N:13][CH:14]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH2:7]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][C:16]2[CH:17]=[C:18]([CH:33]=[CH:34][CH:35]=2)[CH:19]=[C:20]2[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:31])([CH3:32])[CH3:30])=[O:27])[CH2:22][CH2:21]2)=[N:13][CH:14]=1)[CH2:6][CH2:5][C:4]#[CH:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66876269Tert-butyl 4-(3-(5-(5-(trimethylsilyl)pent-4-ynyloxy)pyridin-2-yloxy)benzylidene)piperidine-1-carboxylate

Product 1

HCID 86623921HCID 86623921, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 4-(3-(5-(5-(trimethylsilyl)pent-4-ynyloxy)pyridin-2-yloxy)benzylidene)piperidine-1-carboxylate (0.7 g, 1.34 mmol) in dry THF (4 mL) was added TBAF (3.8 mL, 13.4 mmol) dropwise maintaining ice-cooled conditions. The mixture was stirred for 30 min. The reaction was concentrated and then partitioned between saturated NaHCO3 solution and CH2Cl2. The organic layer was dried over Na2SO4 and concentrated under reduced pressure to give the title compound (0.6 g, 98% yield).

Workup

  1. temperaturecooled conditions
  2. concentrationThe reaction was concentrated
  3. custompartitioned between saturated NaHCO3 solution and CH2Cl2
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a93c18f5acfd46119d30abf582e565f0
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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