HCID 86590984, compound → HCID 69599637, compound

HRID 982657Notes

Reaction equation

HRID 982657 reaction equation
[CH:1]([O:14][C:15](=[O:32])[C@H:16]([N:23]([C:28](=[O:31])[CH:29]=[CH2:30])[O:24][CH2:25]C=C)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(Cl)Cl>[CH:1]([O:14][C:15](=[O:32])[C@H:16]([N:23]1[C:28](=[O:31])[CH:29]=[CH:30][CH2:25][O:24]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

3

Reactant 1

HCID 86590984HCID 86590984, compound

Product 1

HCID 69599637HCID 69599637, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Bis(tricyclohexylphosphine)benzylidene ruthenium dichloride (0.11 g, 0.1289 mmol) was weighed directly into a 50 mL flask, placed under a N2 atmosphere, and dry CH2Cl2 (10 mL) was added, followed by a solution of 6g (1.1020 g, 2.5778 mmol) in dry CH2Cl2 (15 mL). The purple reaction mixture was refluxed for 3 h, an additional 0.11 of catalyst was added, and refluxing was continued for another 2 hours. The mixture was then allowed to cool to room temperature and filtered through a short, densely-packed pad of Silica Gel 60H for thin layer chromatography (φ˜3.8 cm, 1˜2 cm), which was washed with CH2Cl2 (5×20 mL). Evaporation gave a brown oil which was purified via column chromatography (5% EtOAc-hexanes→30% EtOAc-hexanes) to afford 0.500 g (50% yield) of 7g as a brown oil. 1H NMR (400 MHz) in CDCl3 (J, Hz): δ 4.3375 (ddd, 1H, NOCHH), 4.6139 (ddd, 1H, NOCHH), 6.0447 (dt, 1H, NOCH2CH═CH), 6.3715 (s, 1H, NCH), 6.7020 (dt, 1H, NOCH2CH), 6.9626 (s, 1H, CHPh2), 7.10-7.40 (m, 15H, ArH). MS (CI, isobutane), m/z: 400 (M++1).

Workup

  1. temperatureThe purple reaction mixture was refluxed for 3 h
  2. additionan additional 0.11 of catalyst was added
  3. temperaturerefluxing
  4. filtrationfiltered through a short, densely-packed pad of Silica Gel 60H for thin layer chromatography (φ˜3.8 cm, 1˜2 cm), which
  5. washwas washed with CH2Cl2 (5×20 mL)
  6. customEvaporation
  7. customgave a brown oil which
  8. customwas purified via column chromatography (5% EtOAc-hexanes→30% EtOAc-hexanes)

Sources & evidence

ORD record
ord-40320807f68f491aa62f473c9541241a
Source dataset
uspto-grants-2005_03
Patent number
US06861416B2

Reaction notes

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