Sodium Sulfate → HCID 22598007, compound

HRID 1741283Notes

Reaction equation

HRID 1741283 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]([CH3:12])[C:7](OCC)=[O:8].[H-].[H-].[H-].[H-].[Li+].[Al+3].[O-]S([O-])(=O)=O.[Na+].[Na+]>CCOCC>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]([CH3:12])[CH2:7][OH:8]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydride3×HCID 21835134HCID 21835134, compound

Product 1

HCID 22598007HCID 22598007, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent4×

Procedure

To a stirred solution of ethyl 2-(thiazol-2-yl)propanoate (418 mg, 2.3 mmol) in ether (15 ml) at -10° C. was added LiAlH4 (2.2 ml of a 1.0M solution in ether, 2.2 mmol) dropwise. After 2 h at -10° C. more LiAlH4 (0.5 ml of a 1.0M solution in ether, 0.5 mmol) was added. After a further 1 h more LiAlH4 (0.5 ml of a 1.0M solution in ether, 0.5 mmol) was added. Stirring was continued for 1 h then Na2SO4 (sat., 3 ml) was added and the mixture stirred at room temperature for 10 min. The mixture was filtered and the filtrate evaporated. The residue was chromatographed on silica, eluting with CH2Cl2 :MeOH (95:5), to give the alcohol (266 mg, 82%) as a colourless oil. 1H NMR (250 MHz, CDCl3) δ 1.42 (3H, d, J=7.1 Hz), 3.31-3.44 (1H, m), 3.64 (1H, br s), 3.80-3.93 (2H, m), 7.25 (1H, d, J=3.3 Hz), 7.70 (1H, d, J=3.3 Hz).

Workup

  1. stirringthe mixture stirred at room temperature for 10 min
  2. filtrationThe mixture was filtered
  3. customthe filtrate evaporated
  4. customThe residue was chromatographed on silica
  5. washeluting with CH2Cl2 :MeOH (95:5)

Sources & evidence

ORD record
ord-6c4ed6529b43439eaee523fabff0b440
Source dataset
uspto-grants-1999_10
Patent number
US05973156

Reaction notes

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