HCID 25133555, compound → HCID 25129100, compound

HRID 1889127Notes

Reaction equation

HRID 1889127 reaction equation
[CH2:1]([O:4][CH2:5][C@H:6]([O:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH3:16])[CH2:7][CH:8]=[CH2:9])C=C>Cl[Ru](=C1N(C2C(C)=CC(C)=CC=2C)CCN1C1C(C)=CC(C)=CC=1C)(Cl)(=CC1C=CC=CC=1)[P](C1CCCCC1)(C1CCCCC1)C1CCCCC1.C(Cl)Cl>[CH3:16][O:15][CH2:14][CH2:13][O:12][CH2:11][O:10][C@@H:6]1[CH2:7][CH:8]=[CH:9][CH2:1][O:4][CH2:5]1

Participants

4

Reactant 1

HCID 25133555HCID 25133555, compound

Product 1

HCID 25129100HCID 25129100, compoundYield 95.4%

Reagents, catalysts & solvents 2

HCID 178425456HCID 178425456, compoundCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 11 (100 mg, 0.43 mmol) and 2nd generation Grubbs catalyst (18 mg, 0.02 mmol) in CH2Cl2 (10 mL) was heated to 45° C. for 1 h. After this time, the solvent was removed and the residue was purified by flash-chromatography (5:1 CHCl3/EtOAc) to afford 83 mg (94%) of 12 as a colourless oil: 1H NMR (CDCl3) δ 5.87-5.66 (m, 2H), 4.77-4.18 (m, 2H), 4.18-4.14 (m, 2H), 4.01-3.89 (m, 2H), 3.75-3.68 (m, 3H), 3.56-3.53 (m, 2H), 3.38 (s, 3H), 2.54-2.51 (m, 2H); 13C NMR (CDCl3) δ 130.6, 125.9, 94.3, 75.6, 75.1, 71.6, 70.3, 66.8, 58.9, 31.8.

Workup

  1. customAfter this time, the solvent was removed
  2. customthe residue was purified by flash-chromatography (5:1 CHCl3/EtOAc)

Sources & evidence

ORD record
ord-cdc0027484824d1fbdc6d9c4be1cd402
Source dataset
uspto-grants-2013_08
Patent number
US08501961B2

Reaction notes

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