Ethyl chloroformate → Ethyl trans-2-phenylcyclopropanecarboxylate

HRID 271338

Reaction equation

HRID 271338 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

HCID 252496Ethyl trans-2-phenylcyclopropanecarboxylate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8471TriethylamineSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-0463f58e7f0f455a947cb6e71379836b
Source dataset
uspto-grants-2008_11
Patent number
US07452893B2

Linked notes

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