Diethyl Ether → 1-(2,3-Dihydro[1,4]dioxino[2,3-c]pyridin-7-yl)-2-(trimethylsilyl)ethanol

HRID 456609Notes

Reaction equation

HRID 456609 reaction equation
[O:1]1[C:10]2[CH:9]=[C:8]([CH:11]=[O:12])[N:7]=[CH:6][C:5]=2[O:4][CH2:3][CH2:2]1.[CH3:13][Si:14]([CH2:17][Mg]Cl)([CH3:16])[CH3:15].CCOCC>O1CCCC1>[O:1]1[C:10]2[CH:9]=[C:8]([CH:11]([OH:12])[CH2:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[N:7]=[CH:6][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 218736682,3-Dihydro[1,4]dioxino[2,3-c]pyridine-7-carbaldehydeHCID 178418680HCID 178418680, compound

Product 1

HCID 179812561-(2,3-Dihydro[1,4]dioxino[2,3-c]pyridin-7-yl)-2-(trimethylsilyl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of aldehyde (c) (1.2 g) in tetrahydrofuran (20 ml) was treated at 0° C. under argon with a solution of trimethylsilylmethylmagnesium chloride in ether (1M; 8 ml, 8 mmol). After 2 hours the mixture was partitioned between ether—half saturated aqueous ammonium chloride solution. The organic extract was dried and evaporated affording an oil (1.6 g).

Workup

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

Sources & evidence

ORD record
ord-36792a8cf1be4641897458c1edb41685
Source dataset
uspto-grants-2007_03
Patent number
US07186730B2

Reaction notes

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