Methanol → (2-Isopropylthiazol-5-yl)methanol

HRID 52719Notes

Reaction equation

HRID 52719 reaction equation
[CH:1]([C:4]1[S:5][C:6]([C:9](OCC)=[O:10])=[CH:7][N:8]=1)([CH3:3])[CH3:2].CO>C(Cl)(Cl)Cl>[OH:10][CH2:9][C:6]1[S:5][C:4]([CH:1]([CH3:3])[CH3:2])=[N:8][CH:7]=1

Participants

4

Reactant 2

HCID 887Methanol2×HCID 10608068Ethyl 2-isopropylthiazole-5-carboxylate

Product 1

HCID 10820831(2-Isopropylthiazol-5-yl)methanolYield 25%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Using the procedure of Example 5B, but replacing ethyl 2-isopropyl-4-thiazolecarboxylate with ethyl 2-isopropylthiazole-5-carboxylate provided, after silica gel chromatography using 3% methanol in chloroform, the desired compound, Rf 0.3, (5% methanol in chloroform) in 25% yield. 1H NMR (d6 -DMSO) δ1.30 (d, J=7 Hz, 6H), 3.22 (heptet, J=7 Hz, 1H), 4.61 (dd, J=6, 1 Hz, 2H), 5.45 (t, J=6 Hz, 1H), 7.48 (br s, 1H).

Workup

  1. customprovided

Sources & evidence

ORD record
ord-961350f907ce41d59694d731e475ccf6
Source dataset
uspto-grants-1997_04
Patent number
US05616720

Reaction notes

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