Hydrochloric Acid → (Dimethyl-1,3-thiazol-5-yl)methanol

HRID 1532863Notes

Reaction equation

HRID 1532863 reaction equation
C([O:3][C:4]([C:6]1[S:10][C:9]([CH3:11])=[N:8][C:7]=1[CH3:12])=O)C.[H-].C([Al+]CC(C)C)C(C)C.CCCCCC.CCOC(C)=O.Cl>C(Cl)Cl.CO>[CH3:11][C:9]1[S:10][C:6]([CH2:4][OH:3])=[C:7]([CH3:12])[N:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 603810Ethyl 2,4-dimethylthiazole-5-carboxylateHCID 21225700DiisobutylaluminumhydrideHCID 21226206Ethyl acetate hexane

Product 1

HCID 2776250(Dimethyl-1,3-thiazol-5-yl)methanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

A 3-neck 100 mL round-bottom flask under N2 atmosphere was charged with ethyl-2,4-dimethylthiazole-5-carboxylate (1.85 g, 10 mmol ) in anhydrous CH2Cl2 (20 mL). The mixture was cooled to −78° C. 22 mL of di-isobutylaluminum hydride (1.0 M in CH2Cl2) was added dropwise via syringe. The reaction was allowed to warm to room temperature slowly and stirred for 14 h. TLC (1:1 Hexane/EtOAc) showed no starting material. The reaction was cooled to 0° C. MeOH(2 mL) and then 1 M HCl (10 mL) were slowly added. The bath was removed and the reaction stirred for 20 min. Extract with Et2O (3×10 mL). Wash the combined organic layers with brine (10 mL). Dry over MgSO4, filter and remove solvent under vacuum. Yield: 1.363 g (95%), orange oil.

Workup

  1. temperatureto warm to room temperature slowly
  2. temperatureThe reaction was cooled to 0° C
  3. customThe bath was removed
  4. stirringthe reaction stirred for 20 min
  5. extractionExtract with Et2O (3×10 mL)
  6. washWash the combined organic layers with brine (10 mL)
  7. dry with materialDry over MgSO4
  8. filtrationfilter
  9. customremove solvent under vacuum

Sources & evidence

ORD record
ord-8473bf85e8cd41c3a80fa3c6cfcfcf65
Source dataset
uspto-grants-2001_03
Patent number
US06204293B1

Reaction notes

Loading…