Ethyl diazoacetate → HCID 82828030, compound

HRID 2201946Notes

Reaction equation

HRID 2201946 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][CH:3]=1.[N+](=[CH:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N-]>C(Cl)Cl.C([O-])(=O)C.[Rh+2].C([O-])(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 12192Ethyl diazoacetate2×HCID 701194-Bromobenzyl alcohol

Product 1

HCID 82828030HCID 82828030, compound

Reagents, catalysts & solvents 2

HCID 21674Acetic acid, rhodium(2+) saltCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (4-bromophenyl)methanol (1.0 g, 5.35 mmol) in DCM (25 mL) cooled in an ice bath was added rhodium(II) acetate dimmer (0.236 g, 0.535 mmol). To the resulting mixture was slowly added a solution of ethyl diazoacetate (0.721 mL, 6.95 mmol) in DCM (1 mL). The reaction mixture was stirred for 0.5 h. Additional ethyl diazoacetate (300 μL) was added and the resulting mixture was stirred for an additional 0.5 h. The mixture was concentrated and the residue was purified by chromatography (0, 5, 10, 15% EtOAc/Hexanes) to give the title compound. LCMS m/z=273.2 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.21 (t, J=7.1 Hz, 3H), 4.12-4.15 (m, 2H), 4.16 (s, 2H), 4.52 (s, 2H), 7.31 (d, J=8.3 Hz, 2H), 7.55 (d, J=8.3 Hz, 2H).

Workup

  1. stirringthe resulting mixture was stirred for an additional 0.5 h
  2. concentrationThe mixture was concentrated
  3. customthe residue was purified by chromatography (0, 5, 10, 15% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-14c0e8e6baa744ab92166c9ddad412e7
Source dataset
uspto-grants-2016_06
Patent number
US09365511B2

Reaction notes

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