ChemicalBook CAS DataBase List 4-Hydroxymethylthiazole

4-Hydroxymethylthiazole synthesis

5synthesis methods

Product Name:4-Hydroxymethylthiazole
CAS Number:7036-04-6
Molecular formula:C4H5NOS
Molecular Weight:115.15

3364-80-5
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$11.00/250mg

7036-04-6
134 suppliers
$26.00/250mg

Yield: 74.3%

Reaction Conditions:

with methanol;sodium tetrahydroborate at 0; for 1 h;

Steps:

40.1 Thiazol-4-ylmethanol
To a solution of thiazole-4-carboxaldehyde (0.810 ml, 9.67 mmol, Combi-Blocks Inc.) in MeOH (48.3 ml) at 0 °C was added sodium borohydride (0.341 ml, 9.67 mmol, Sigma-Aldrich Chemical Company, Inc.) in portions. The reaction mixture was allowed to stir for 1 hour. Saturated aqueous ammonium chloride solution was carefully added and the reaction mixture was filtered. The filtrate was concentrated in vacuo. The solid was taken up in 10% MeOH/DCM and filtered through a plug of silica gel to provide thiazol- 4-ylmethanol (0.826 g, 7.18 mmol, 74.3% yield) as a yellow oil. MS m/z = 116.0 [M+H]⁺. Calculated for C₄H₅NOS: 115.009. H NMR (400 MHz, CHLOROFORM -J) δ ppm 2.58 (br. s., 1 H) 4.86 (s, 2 H) 7.27 - 7.30 (m, 1 H) 8.83 (d, J=l .76 Hz, 1 H)

References:

AMGEN INC.;MINATTI, Ana Elena;LOW, Jonathan, D.;ALLEN, Jennifer, R.;AMEGADZIE, Albert;BROWN, James;FROHN, Michael, J.;GUZMAN-PEREZ, Angel;HARRINGTON, Paul, E.;LOPEZ, Patricia;MA, Vu Van;NISHIMURA, Nobuko;QIAN, Wenyuan;RUMFELT, Shannon;RZASA, Robert, M.;SHAM, Kelvin;SMITH, Adrian, L.;WHITE, Ryan;XUE, Qiufen WO2014/138484, 2014, A1 Location in patent:Page/Page column 167; 168