Ethyl chloroformate → Ethyl trans-2-phenylcyclopropanecarboxylate

HRID 271338

反応式

HRID 271338 の反応式
[C:1]1([C@@H:7]2[CH2:9][C@H:8]2[C:10]([OH:12])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC(O[CH2:17][CH3:18])=O>CN(C)C1C=CN=CC=1.C(N(CC)CC)C>[CH2:17]([O:11][C:10]([C@@H:8]1[CH2:9][C@H:7]1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:12])[CH3:18]

参加物

5

反応物 2

HCID 10928Ethyl chloroformateHCID 237413trans-2-Phenylcyclopropanecarboxylic acid2 回

生成物 1

HCID 252496Ethyl trans-2-phenylcyclopropanecarboxylate

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 8471Triethylamine溶媒

実験手順

To an ice cold solution of 1.62 g of (1R, 2R)-2-phenyl-cyclopropane carboxylic acid (from racemic trans-2-phenyl-cyclopropane carboxylic acid by resolution on a chiral HPLC column) and 2.0 mL of triethylamine and 0.12 g of 4-dimethylaminopyridine was added 1.2 mL of ethyl chloroformate The mixture was allowed to warm and stir for 1 h, then washed with 25 mL of 3N HCl, 25 mL of water, 25 mL of saturated sodium carbonate and dried over magnesium sulfate. Removal of solvents under reduced pressure gave 1.9 g of product as an oil: MS (m+1)=191.1; 1H NMR (400 MHz, CDCl3) 7.3 (dd, 2H), 7.2 (t, 1H), 7.1 (d, 2H), 4.18 (q, 2H), 2.5 (m, 1H), 1.9 (m, 1H), 1.6 (m, 1H), 1.3 (overlapping m and t, 4H).

後処理

  1. temperatureto warm
  2. washwashed with 25 mL of 3N HCl, 25 mL of water, 25 mL of saturated sodium carbonate
  3. dry with materialdried over magnesium sulfate
  4. customRemoval of solvents under reduced pressure

出典と根拠

ORDレコード
ord-0463f58e7f0f455a947cb6e71379836b
出典データセット
uspto-grants-2008_11
特許番号
US07452893B2

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