Diethyl Ether → (2-Cyclopropylthiazol-4-yl)methanol

HRID 1654211Notes

Reaction equation

HRID 1654211 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].CCOCC.[CH:12]1([C:15]2[S:16][CH:17]=[C:18]([C:20](OCC)=[O:21])[N:19]=2)[CH2:14][CH2:13]1>O.C(OCC)(=O)C>[CH:12]1([C:15]2[S:16][CH:17]=[C:18]([CH2:20][OH:21])[N:19]=2)[CH2:14][CH2:13]1

Participants

6

Reactant 3

HCID 3283Diethyl Ether2×HCID 18771956Ethyl 2-cyclopropylthiazole-4-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 20079576(2-Cyclopropylthiazol-4-yl)methanolYield 72.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of lithium aluminium hydride (0.32 g) and anhydrous ether (40 ml) was added dropwise an anhydrous ether (10 ml) solution of ethyl 2-cyclopropyl-4-thiazolecarboxylate (1.65 g), followed by stirring for one hour at room temperature. To the reaction mixture was added dropwise water (20 ml) under cooling with ice to decompose excess amount of the reducing agent. To the resultant mixture were added ethyl acetate (50 ml) and water (25 ml), followed by extraction with ethyl acetate. The organic layer was washed with water (25 ml) and a saturated aqueous solution of sodium chloride (25 ml), successively, followed by drying over magnesium sulfate. The solvent was distilled off, and the residue was subjected to a silica gel chromatography (2.5×30 cm), eluting with ethyl acetate-hexane (2:1). The desired fraction was concentrated to give 2-cyclopropyl-4-hydroxymethyl thiazole (0.94 g) as pale yellow needles. 1H-NMR (CDCl3) δ: 0.98~1.18(4H,m), 2.24~2.39(1H,m), 3.20(1H,bs.), 4.70(2H,d,J=5 Hz), 6.93(1H,s)

Workup

  1. temperatureunder cooling with ice
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water (25 ml)
  4. dry with materialby drying over magnesium sulfate
  5. distillationThe solvent was distilled off
  6. washeluting with ethyl acetate-hexane (2:1)
  7. concentrationThe desired fraction was concentrated

Sources & evidence

ORD record
ord-2ae6c6c4fa814cff82bd2663217298d3
Source dataset
uspto-grants-1995_04
Patent number
US05405861

Reaction notes

Loading…