1-(2,3-Dihydro[1,4]dioxino[2,3-c]pyridin-7-yl)-2-(trimethylsilyl)ethanol → 7-Ethenyl-2,3-dihydro[1,4]dioxino[2,3-c]pyridine

HRID 456610Notes

Reaction equation

HRID 456610 reaction equation
[O:1]1[C:10]2[CH:9]=[C:8]([CH:11](O)[CH2:12][Si](C)(C)C)[N:7]=[CH:6][C:5]=2[O:4][CH2:3][CH2:2]1.CC(C)([O-])C.[K+]>O1CCCC1>[CH:11]([C:8]1[N:7]=[CH:6][C:5]2[O:4][CH2:3][CH2:2][O:1][C:10]=2[CH:9]=1)=[CH2:12]

Participants

4

Reactant 2

HCID 179812561-(2,3-Dihydro[1,4]dioxino[2,3-c]pyridin-7-yl)-2-(trimethylsilyl)ethanolHCID 23665647Potassium tert-butoxide

Product 1

HCID 179812417-Ethenyl-2,3-dihydro[1,4]dioxino[2,3-c]pyridineYield 145.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (d) (1.6 g) in tetrahydrofuran (20 ml) was treated at 0° C. under argon with a solution of potassium t-butoxide in tetrahydrofuran (1M; 7.6 ml, 7.6 mmol). After 2 hours the mixture was partitioned between ethyl acetate—half saturated aqueous ammonium chloride solution. The organic extract was dried and evaporated affording an oil (1.5 g).

Workup

  1. customAfter 2 hours the mixture was partitioned between ethyl acetate—half saturated aqueous ammonium chloride solution
  2. extractionThe organic extract
  3. customwas dried
  4. customevaporated

Sources & evidence

ORD record
ord-786376f0cc7b4dfb84dbbfb07c033888
Source dataset
uspto-grants-2007_03
Patent number
US07186730B2

Reaction notes

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