HCID 84740921, compound → HCID 77230809, compound

HRID 409026Notes

Reaction equation

HRID 409026 reaction equation
[Cl:1][C:2]1[S:13][C:5]2=[N:6][C:7]([Cl:12])=[C:8]([CH:10]=[O:11])[CH:9]=[C:4]2[CH:3]=1.[CH3:14][Mg]Cl>C1COCC1>[Cl:1][C:2]1[S:13][C:5]2=[N:6][C:7]([Cl:12])=[C:8]([CH:10]([OH:11])[CH3:14])[CH:9]=[C:4]2[CH:3]=1

Participants

4

Reactant 2

HCID 84740921HCID 84740921, compoundHCID 178418332HCID 178418332, compound2×

Product 1

HCID 77230809HCID 77230809, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a reaction flask containing 2,6-dichlorothieno[2,3-b]pyridine-5-carbaldehyde (5.1 g, 21.97 mmol) in 300 mL of THF at −20° C. was added methylmagnesium chloride, 3.0M solution in tetrahydrofuran (7.69 mL, 23.07 mmol) dropwise. After 1 h, an additional charge of 0.7 mL of MeMgCl was added. After 15 min, the reaction was quenched by the addition of 50 mL sat. NH4Cl and 50 mL water. After warming to rt, ethyl acetate was added and the organic layer was separated and washed with water and brine. The organic layer was dried over MgSO4, filtered, and concentrated to afford 1-(2,6-dichlorothieno[2,3-b]pyridin-5-yl)-ethanol. 1H NMR (400 MHz, CDCl3) δ 8.19 (d, J=0.8 Hz, 1H), 7.14 (s, 1H), 5.32 (qdd, J=6.3, 3.5, 0.8 Hz, 1H), 2.07 (J=3.5 Hz, 1H), 1.56 (d, J=6.6 Hz, 3H) ppm.

Workup

  1. additionwas added
  2. waitAfter 15 min
  3. customthe reaction was quenched by the addition of 50 mL sat. NH4Cl and 50 mL water
  4. additionethyl acetate was added
  5. customthe organic layer was separated
  6. washwashed with water and brine
  7. dry with materialThe organic layer was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-693126ca621b4ae8a1f2f5607ce3f9cb
Source dataset
uspto-grants-2014_06
Patent number
US08759371B2

Reaction notes

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