2-Propanone, 1-(acetyloxy)-3-chloro- → (2-(Chloromethyl)-1,3-dioxolan-2-yl)methyl acetate

HRID 28375

反応式

HRID 28375 の反応式
[C:1]([O:4][CH2:5][C:6]([CH2:8][Cl:9])=[O:7])(=[O:3])[CH3:2].C[Si](C)(C)[O:12][CH2:13][CH2:14]O[Si](C)(C)C.C(=O)=O.CC(C)=O>C(Cl)Cl.FC(F)(F)S(O[Si](C)(C)C)(=O)=O>[C:1]([O:4][CH2:5][C:6]1([CH2:8][Cl:9])[O:12][CH2:13][CH2:14][O:7]1)(=[O:3])[CH3:2]

参加物

6

反応物 3

HCID 384132-Propanone, 1-(acetyloxy)-3-chloro-HCID 818582,2,7,7-Tetramethyl-3,6-dioxa-2,7-disilaoctaneHCID 18522661Acetone cardice

生成物 1

HCID 57426437(2-(Chloromethyl)-1,3-dioxolan-2-yl)methyl acetate収率 73.6%

試薬・触媒・溶媒 2

HCID 65367Trimethylsilyl triflate触媒HCID 6344Dichloromethane溶媒

実験手順

A solution of 1-acetoxy-3-chloroacetone (20.0 g, 133 mmol, TCI America) and 1,2-bis(trimethylsilyloxy)ethane (30.2 g, 146 mmol, Aldrich) in anhydrous CH2Cl2 and under N2 atmosphere was cooled (−78° C., dry ice/acetone) and trimethylsilyl trifluoromethanesulfonate (1.2 mL, 6.6 mmol, Aldrich) was added. The reaction was warmed to room temperature and stirred for 5 days, with monitoring by 1H-NMR. The crude reaction solution was separated by silica gel column, and eluted with CH2Cl2, then 5% Et2O in CH2Cl2. Product fractions were pooled and concentrated in-vacuo giving the title compound (19.05 g) as a yellow oil, contaminated with 1-acetoxy-3-chloroacetone (2.93 g) and CH2Cl2 (1.0 g): 1H NMR (500 MHz, CDCl3) δ ppm 4.17 (2H, s), 4.03-4.11 (4H, m), 3.60 (2H, s), 2.09 (3H, s).

後処理

  1. additionwas added
  2. customThe crude reaction solution
  3. customwas separated by silica gel column
  4. washeluted with CH2Cl2
  5. concentrationconcentrated in-vacuo

出典と根拠

ORDレコード
ord-5d244ae256144dc1b9ac39ab572691d6
出典データセット
uspto-grants-2008_09
特許番号
US07419969B2

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