Tetrabutylammonium Fluoride → HCID 86627925, compound

HRID 2241000Notes

Reaction equation

HRID 2241000 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][Si](C(C)C)(C(C)C)C(C)C)=[CH:4][C:3]=1[N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[CH:4]=1)#[CH:9]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 575824344-(2-Fluoro-5-((triisopropylsilyl)ethynyl)phenyl)morpholine

Product 1

HCID 86627925HCID 86627925, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 25 mL round bottom flask was charged with 4-(2-fluoro-5-((triisopropylsilyl)ethynyl)phenyl)morpholine (0.540 g, 1.50 mmol), diluted with tetrahydrofuran (THF, 1.5 ml) at room temperature. A 1M solution of tetrabutylammonium fluoride in THF (2.0 mL) was added. After 105 minutes reaction the mixture was partitioned between ethylacetate and water, separated, dried with sodium sulfate, and concentrated to an oil by rotary evaporation to yield 0.305 g of 4-(5-ethynyl-2-fluorophenyl)morpholine.

Workup

  1. customAfter 105 minutes reaction the mixture
  2. customwas partitioned between ethylacetate and water
  3. customseparated
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated to an oil by rotary evaporation

Sources & evidence

ORD record
ord-1153f7c182ca4a20a09764d84d235b59
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Reaction notes

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