Citric Acid → HCID 178472501、化合物

HRID 1968942ノート

反応式

HRID 1968942 の反応式
Cl[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].[OH:9][CH:10]1[CH2:15][CH2:14][CH:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12][CH2:11]1.N1C=CN=C1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O>[CH3:6][C:5]([Si:2]([CH3:4])([CH3:3])[O:9][C@H:10]1[CH2:11][CH2:12][C@H:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:14][CH2:15]1)([CH3:8])[CH3:7]

参加物

6

反応物 4

HCID 311Citric AcidHCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 86973Ethyl 4-hydroxycyclohexanecarboxylate

生成物 1

HCID 178472501HCID 178472501、化合物収率 101.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
40 °C

実験手順

Chloro(1,1-dimethylethyl)dimethylsilane (115 g; 0.76 mol) was added in portions over 1 hour to a solution of commercially available ethyl 4-hydroxycyclohexanecarboxylate (118 g; 0.68 mol), imidazole (103 g; 1.52 mol) and dimethylformamide (400 mL) stirred under an atmosphere of argon. A small exotherm was observed resulting in the reaction mixture temperature increasing to ˜40° C. The mixture was stirred at room temperature overnight then poured into 10% citric acid solution (2 L) and extracted with diethyl ether (2×800 mL). The ether extracts were washed with water, brine and then dried (Na2SO4) and the solvent was removed to give the title compound as an oil (198.4 g)

後処理

  1. customA small exotherm was observed resulting in the reaction mixture temperature
  2. stirringThe mixture was stirred at room temperature overnight
  3. extractionextracted with diethyl ether (2×800 mL)
  4. washThe ether extracts were washed with water, brine
  5. dry with materialdried (Na2SO4)
  6. customthe solvent was removed

出典と根拠

ORDレコード
ord-c7ad5c44b5ec4e12b6ab0641c5e8de22
出典データセット
uspto-grants-2013_04
特許番号
US08426443B2

反応ノート

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