Ethylene Glycol → 2-Bromo-5-(2-methyl-[1,3]dioxolan-2-yl)-thiazole

HRID 42837

Reaction equation

HRID 42837 reaction equation
N#N.[Br:3][C:4]1[S:5][C:6]([C:9](=[O:11])[CH3:10])=[CH:7][N:8]=1.[CH2:12](O)[CH2:13][OH:14].COC(OC)OC>C([O-])(O)=O.[Na+]>[Br:3][C:4]1[S:5][C:6]([C:9]2([CH3:10])[O:14][CH2:13][CH2:12][O:11]2)=[CH:7][N:8]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 947NitrogenHCID 9005Trimethyl orthoformateHCID 575628131-(2-Bromo-1,3-thiazol-5-yl)ethan-1-one

Product 1

HCID 668200782-Bromo-5-(2-methyl-[1,3]dioxolan-2-yl)-thiazole

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
95 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and a condenser under inert atmosphere (N2), a solution of 1-(2-bromo-thiazol-5-yl)-ethanone (2.20 g, 10.68 mmol) in ethylene glycol (11.46 mL, 205.53 mmol) was treated with trimethylorthoformate (2.39 mL, 21.76 mmol) followed by LiBF4 (204 mg, 2.14 mmol). The reaction mixture was heated at 95° C. for 2 days. Sat. aq. NaHCO3 (50 mL) was added and the mixture was extracted with EA (50 mL). The org. extracts were washed with brine (2×50 mL), dried over MgSO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (20:1 to 3:1 hept-EA) gave the title compound as a yellow oil. TLC:rf (1:1 hept-EA)=0.80. LC-MS-conditions 01: tR=0.84 min; [M+H]+=251.85.

Workup

  1. extractionthe mixture was extracted with EA (50 mL)
  2. washextracts were washed with brine (2×50 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customPurification of the residue by FC (20:1 to 3:1 hept-EA)

Sources & evidence

ORD record
ord-47e77418a6244000a6972217938b3779
Source dataset
uspto-grants-2013_09
Patent number
US08536209B2

Linked notes

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