Nitrogen → [5-(2-Methyl-[1,3]dioxolan-2-yl)-thiazol-2-yl]-methanol

HRID 1044755Notes

Reaction equation

HRID 1044755 reaction equation
N#N.[CH3:3][C:4]1([C:9]2[S:13][C:12]([CH:14]=[O:15])=[N:11][CH:10]=2)[O:8][CH2:7][CH2:6][O:5]1.[BH4-].[Na+].O>CO>[CH3:3][C:4]1([C:9]2[S:13][C:12]([CH2:14][OH:15])=[N:11][CH:10]=2)[O:8][CH2:7][CH2:6][O:5]1

Participants

6

Reactant 4

HCID 947NitrogenHCID 962WaterHCID 4311764Sodium borohydrideHCID 866494885-(2-Methyl-[1,3]dioxolan-2-yl)-thiazole-2-carbaldehyde

Product 1

HCID 66819954[5-(2-Methyl-[1,3]dioxolan-2-yl)-thiazol-2-yl]-methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), 5-(2-methyl-[1,3]dioxolan-2-yl)thiazole-2-carbaldehyde (5.12 g, 25.70 mmol) was dissolved in MeOH (60 mL). NaBH4 (1.26 g, 31.89 mmol) was added portionwise at 0° C. and the reaction mixture stirred at 0° C. for 1 h. Water was added and the mixture extracted with EA (3×). The combined org. extracts were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure to give the title compound as an orange oil. TLC:rf (1:1 hept-EA)=0.31. LC-MS-conditions 02: tR=0.64 min; [M+H]+=202.52.

Workup

  1. extractionthe mixture extracted with EA (3×)
  2. dry with materialextracts were dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-fb31cfd042f04b1285153e949d2eb794
Source dataset
uspto-grants-2013_10
Patent number
US08563714B2

Reaction notes

Loading…