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

HRID 42797

反応式

HRID 42797 の反応式
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

参加物

6

反応物 4

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

生成物 1

HCID 669288134-Chloromethyl-2-(2-methyl-[1,3]dioxolan-2-yl)-thiazole

試薬・触媒・溶媒 1

HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
95 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-d2bbcdd6662c4b628c613255c016266f
出典データセット
uspto-grants-2013_09
特許番号
US08536209B2

関連ノート

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