3-Bromobut-1-ene → (E)-5-bromo-1-(3,3-diethoxypropoxy)-2-methylpent-2-ene

HRID 1472755Notes

Reaction equation

HRID 1472755 reaction equation
[Br:1][CH:2](C)[CH:3]=C.[CH2:6]([O:8][CH:9]([O:17][CH2:18][CH3:19])[CH2:10][CH2:11][O:12][CH2:13][C:14]([CH3:16])=[CH2:15])[CH3:7]>Cl[Ru](=C1N(C2C(C)=CC(C)=CC=2C)CCN1C1C(C)=CC(C)=CC=1C)(Cl)(=CC1C=CC=CC=1)[P](C1CCCCC1)(C1CCCCC1)C1CCCCC1>[Br:1][CH2:2][CH2:3]/[CH:15]=[C:14](\[CH3:16])/[CH2:13][O:12][CH2:11][CH2:10][CH:9]([O:8][CH2:6][CH3:7])[O:17][CH2:18][CH3:19]

Participants

4

Reactant 2

HCID 1408763-Bromobut-1-eneHCID 866764593-(3,3-Diethoxypropoxy)-2-methylprop-1-ene

Product 1

HCID 86676460(E)-5-bromo-1-(3,3-diethoxypropoxy)-2-methylpent-2-eneYield 9%

Reagents, catalysts & solvents 1

HCID 178425456HCID 178425456, compoundCatalyst

Procedure

To previously nitrogen degassed DCM (18 mL) was added Second Generation Grubbs Catalyst (0.225 g, 0.30 mmol) followed by 3-bromobutene (2.03 g, 15.0 mmol) and 3-(3,3-diethoxypropoxy)-2-methylprop-1-ene (1.52 g, 7.52 mmol). The reaction mixture was further degassed for 5 minutes and then heated under reflux for 2 hours. The solvent was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography eluting with 0-100% ethyl acetate in iso-hexane to afford the title compound (0.208 g, 9%).

Workup

  1. customTo previously nitrogen degassed DCM (18 mL)
  2. customThe reaction mixture was further degassed for 5 minutes
  3. temperatureheated
  4. temperatureunder reflux for 2 hours
  5. concentrationThe solvent was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography
  7. washeluting with 0-100% ethyl acetate in iso-hexane

Sources & evidence

ORD record
ord-e7836cc0af1e405fb3940df8ece9e328
Source dataset
uspto-grants-2015_04
Patent number
US09012644B2

Reaction notes

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