1-Hexene → HCID 15956438, compound

HRID 1271409Notes

Reaction equation

HRID 1271409 reaction equation
[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH3:6].[Br:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=[O:17])[C:11]2=[N+]=[N-]>ClCCl.C([O-])(=O)C.[Rh+2].C([O-])(=O)C>[Br:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=[O:17])[C:11]12[CH2:1][CH:2]1[CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 2

HCID 115971-HexeneHCID 178514318HCID 178514318, compound

Product 1

HCID 15956438HCID 15956438, compoundYield 70%

Reagents, catalysts & solvents 2

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

Procedure

A solution containing 1-hexene (10 equiv.) and 1 mol % of rhodium (II) acetate in dry dichloromethane (10 mL) was degasified under an argon atmosphere. To this reaction mixture, a solution of 5-bromo-3-diazo-oxindole (1 equiv.) (J. Am. Chem. Soc. 1958, 80, 2257–2263) was added dropwise slowly over 1 h under an argon atmosphere at room temperature. The reaction mixture was stirred for 16 hours at room temperature, and concentrated to dryness in vacuo. The solid residue was chromatographed using hexane and ethyl acetate (v/v 1:1) as eluent. The chromatographed material gave the title compound in 70% yield. MS: m/z 294.3 [M+1]+. 1H NMR (CCl3D): δ 8.32 (br, 1H), 7.25 (d, 1H), 6.89 (d, 1H), 6.78 (d, 1H), 1.89 (m, 2H), 1.65 (m, 1H), 1.51 (m, 2H), 1.18–1.31 (m, 4H), 0.79 (t, 3H).

Workup

  1. concentrationconcentrated to dryness in vacuo
  2. customThe solid residue was chromatographed

Sources & evidence

ORD record
ord-49dad2369dd744acb704147676cbd560
Source dataset
uspto-grants-2007_04
Patent number
US07205328B2

Reaction notes

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