Ethyl chloroformate → Ethyl trans-2-phenylcyclopropanecarboxylate

HRID 271338

반응식

HRID 271338 반응식
[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]

참가 물질

5

반응물 2

HCID 10928Ethyl chloroformateHCID 237413trans-2-Phenylcyclopropanecarboxylic acid2회

생성물 1

HCID 252496Ethyl trans-2-phenylcyclopropanecarboxylate

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8471Triethylamine용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-0463f58e7f0f455a947cb6e71379836b
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452893B2

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