Ethyl diazoacetate → 3-Fluorobenzyloxyacetic Acid Ethyl Ester

HRID 2053595Notes

Reaction equation

HRID 2053595 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].[N+](=[CH:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N-]>ClCCl.CCCCCCC.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[CH2:16]([O:15][C:13](=[O:14])[CH2:12][O:6][CH2:5][C:4]1[CH:7]=[CH:8][CH:9]=[C:2]([F:1])[CH:3]=1)[CH3:17]

Participants

6

Reactant 2

HCID 12192Ethyl diazoacetateHCID 680083-Fluorobenzylic alcohol

Product 1

HCID 685689803-Fluorobenzyloxyacetic Acid Ethyl EsterYield 98.4%

Reagents, catalysts & solvents 3

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

Procedure

To a solution of 3-fluorobenzyl alcohol (1.12 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 1.88 g of the product 392. 1H NMR (CDCl3) δ 7.30 (m, 1H), 7.12 (m, 2H), 6.99 (dt, 1H), 4.63 (s, 2H), 4.28 (q, 2H), 4.11 (s, 2H), 1.30 (t, 3H); MS: m/z 213 (M++1).

Workup

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

Sources & evidence

ORD record
ord-5320972d59aa4a6691e303ee15b7f855
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Reaction notes

Loading…