Ethyl diazoacetate → (3-Trifluoromethylbenzyloxy)acetic Acid Ethyl Ester

HRID 2053596Notes

Reaction equation

HRID 2053596 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][OH:7].[N+](=[CH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N-]>ClCCl.CCCCCCC.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[CH2:19]([O:18][C:16](=[O:17])[CH2:15][O:7][CH2:6][C:5]1[CH:8]=[CH:9][CH:10]=[C:3]([C:2]([F:11])([F:12])[F:1])[CH:4]=1)[CH3:20]

Participants

6

Reactant 2

HCID 12192Ethyl diazoacetateHCID 676813-(Trifluoromethyl)benzylic alcohol

Product 1

HCID 68572230(3-Trifluoromethylbenzyloxy)acetic Acid Ethyl EsterYield 97.9%

Reagents, catalysts & solvents 3

HCID 423677Acetic acid, rhodium salt (4:2)CatalystHCID 6344DichloromethaneSolventHCID 8900HeptaneSolvent

Procedure

To a solution of 3-trifluoromethylbenzyl alcohol (1.62 g, 10.0 mmol) in dichloromethane (20 mL) is added rhodium (II) acetate dimer (10 mg) followed by ethyl diazoacetate (0.95 mL, 9.0 mmol). The reaction mixture is stirred at RT for 30 min. The reaction mixture is diluted with heptane, filtered through celite, and the filtrate is evaporated and the residue is vacuum distilled at 150° C. to give 2.31 g of the product 394. 1H NMR (CDCl3) δ 7.65 (bs, 1H), 7.57 (m, 2H), 7.48 (t, 1H), 4.69 (s, 2H), 4.24 (q, 2H), 4.14 (s, 2H), 1.30 (t, 3H); MS: m/z 263 (M+).

Workup

  1. filtrationfiltered through celite
  2. customthe filtrate is evaporated
  3. distillationdistilled at 150° C.

Sources & evidence

ORD record
ord-5d15415e84004d42b26d11141b4ccaa5
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Reaction notes

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