HCID 59300355, compound → HCID 59299825, compound

HRID 2236504Notes

Reaction equation

HRID 2236504 reaction equation
[C:1]([O:5][C:6](=[O:22])[N:7]([CH2:19][CH:20]=[CH2:21])[CH:8]([C:12]1[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=1)[CH2:9]C=C)([CH3:4])([CH3:3])[CH3:2]>C(Cl)Cl.Cl[Ru](=CC1C=CC=CC=1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)Cl>[C:1]([O:5][C:6]([N:7]1[CH2:19][CH:20]=[CH:21][CH2:9][CH:8]1[C:12]1[CH:13]=[CH:14][C:15]([Br:18])=[CH:16][CH:17]=1)=[O:22])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 59300355HCID 59300355, compound

Product 1

HCID 59299825HCID 59299825, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 178479819HCID 178479819, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Allyl-[1-(4-bromo-phenyl)-but-3-enyl]-carbamic acid tert-butyl ester (300 mg, 0.82 mmol) in CH2Cl2 (10 mL) is degassed and the 2nd generation of Grubb's catalyst (40 mg, 5%) is added under N2. The reaction did not proceed at room temperature and the mixture is brought to reflux. TLC is used to determine complete reaction of the olefin. The mixture is loaded onto a column and purified to provide the desired product (208 mg, 75%). 1H NMR (300 MHz, CDCl3) ∂7.43(2H, d, J=8.1 Hz), 7.17-7.26 (2H, m), 5.89-5.95 (1H, m), 5.34-5.58 (2H, m), 4.14-4.36 (1H, m), 3.35-3.44 (1H, m), 2.73-2.81 (1H, m), 2.41-2.62 (1H, m), 1.48 (9H, s).

Workup

  1. customdid not proceed at room temperature
  2. temperatureto reflux
  3. custompurified

Sources & evidence

ORD record
ord-a9346d22013a40f994f7981008c7f47c
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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