Acetic Acid → HCID 71152016, compound

HRID 2174185Notes

Reaction equation

HRID 2174185 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[S:5][C:6]=1[CH:7]=[O:8].[CH3:15][Mg]Cl.O.CC(O)=O>C1COCC1>[Cl:1][C:2]1[N:3]=[C:4]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[S:5][C:6]=1[CH:7]([OH:8])[CH3:15]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 21643578HCID 21643578, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 71152016HCID 71152016, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

4-Chloro-2-(3-pyridyl)thiazole-5-carbaldehyde (1.4 g, 6.25 mmol) was dissolved in dry THF (28 ml) and cooled to −10° C. A 3 M solution of methyl magnesiumchloride in THF (2.08 ml, 6.25 mmol) was added dropwise. The reaction mixture was stirred at ambient temperature for 18 hours. Water (1.7 ml) was added, followed by CH3COOH (1 ml). The reaction mixture was extracted with ethyl acetate, the organic layer was separated, dried, filtered, and the solvent was evaporated to dryness to get 1-[4-chloro-2-(3-pyridyl)thiazol-5-yl]ethanol as a brown solid. 1H NMR (300 Mz, DMSO-d6): δ: 9.07 (s, 1H), 8.68 (dd, 1H, J=1.5 Hz), 8.26 (m, 1H), 7.53 (m, 1H), 5.92 (t, 1H, J=6 Hz), 4.67 (d, 3H, J=5.4 Hz).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. customthe organic layer was separated
  3. customdried
  4. filtrationfiltered
  5. customthe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-0e5a4fa8990347caa6465148d47b4d1a
Source dataset
uspto-grants-2015_06
Patent number
US09060519B2

Reaction notes

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