Ethylene Glycol → 4-Chloromethyl-2-(2-methyl-[1,3]dioxolan-2-yl)-thiazole

HRID 42797

반응식

HRID 42797 반응식
N#N.[Cl:3][CH2:4][C:5]1[N:6]=[C:7]([C:10](=[O:12])[CH3:11])[S:8][CH:9]=1.[CH2:13](O)[CH2:14][OH:15].COC(OC)OC>C([O-])(O)=O.[Na+]>[Cl:3][CH2:4][C:5]1[N:6]=[C:7]([C:10]2([CH3:11])[O:15][CH2:14][CH2:13][O:12]2)[S:8][CH:9]=1

참가 물질

6

반응물 4

HCID 174Ethylene GlycolHCID 947NitrogenHCID 9005Trimethyl orthoformateHCID 668199771-(4-Chloromethyl-thiazol-2-yl)ethanone

생성물 1

HCID 669288134-Chloromethyl-2-(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 Dean-Stark apparatus under inert atmosphere (N2), a solution of 1-(4-chloromethyl-thiazol-2-yl)-ethanone (992 mg, 5.65 mmol) in ethylene glycol (6.30 mL, 112.96 mmol) was treated with trimethylorthoformate (1.24 mL, 11.30 mmol) followed by LiBF4 (106 mg, 1.13 mmol). The reaction mixture was heated at 95° C. for 2 h. 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 (4:1 hept-EA) gave the title compound as a yellow oil: TLC:rf (4:1 hept-EA)=0.30. LC-MS-conditions 02: tR=0.84 min, [M+H]+=220.36.

후처리

  1. customIn a flame dried round-bottomed flask equipped with a magnetic stir bar
  2. extractionthe mixture was extracted with EA (50 mL)
  3. washextracts were washed with brine (2×50 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure
  7. customPurification of the residue by FC (4:1 hept-EA)

출처 및 근거

ORD 기록
ord-d2bbcdd6662c4b628c613255c016266f
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536209B2

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