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

HRID 42837

반응식

HRID 42837 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 516892Sodium Bicarbonate용매

반응 조건

온도
95 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-47e77418a6244000a6972217938b3779
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536209B2

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