2-Bromopropene → Isoprene 5-isopropenyl-6-methoxy-2,3-dihydro-benzo[1,4]dioxine

HRID 2266128

Reaktionsgleichung

Reaktionsgleichung von HRID 2266128
Br[C:2]([CH3:4])=[CH2:3].[CH3:5][O:6][C:7]1[CH:16]=[CH:15][C:10]2[O:11][CH2:12][CH2:13][O:14][C:9]=2[C:8]=1B(O)O.[C:20]([O-])([O-])=O.[K+].[K+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:2]([C:8]1[C:9]2[O:14][CH2:13][CH2:12][O:11][C:10]=2[CH:15]=[CH:16][C:7]=1[O:6][CH3:5])([CH3:4])=[CH2:3].[CH2:10]=[CH:15][C:16](=[CH2:7])[CH3:20]

Komponenten

6

Edukt 3

HCID 112022-BromopropeneHCID 11430Potassium CarbonateHCID 225718926-Methoxy-2,3-dihydro-benzo[1,4]dioxin-5-yl-boronic acid

Produkt 1

HCID 86600725Isoprene 5-isopropenyl-6-methoxy-2,3-dihydro-benzo[1,4]dioxine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-bromopropene (5.4 ml, 59 mmol) in 200 mL DME was added Pd(Ph3P)4 (3.116, 2.8 mmol). After 30 min 6-methoxy-2,3-dihydro-benzo[1,4]dioxin-5-yl-boronic acid (13.320 g, 58.6 mmol) and K2CO3 (8.099 g, 58.6 mmol) was added. The mixture was warmed to reflux. After 16 hours the mixture was cooled, filtered through a pad of celite and concentrated in vacuo. The residue was dissolved in H2O and extracted with ethyl acetate. The combined organics were washed with saturated NaHCO3, dried over MgSO4, filtered and concentrated in vacuo. Purification via flash chromatography afforded isoprene 5-isopropenyl-6-methoxy-2,3-dihydro-benzo[1,4]dioxine (5.542 g, as an inseparable mixture of product/sm 1:1) as an oil.

Aufarbeitung

  1. temperatureThe mixture was warmed to reflux
  2. temperatureAfter 16 hours the mixture was cooled
  3. filtrationfiltered through a pad of celite
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in H2O
  6. extractionextracted with ethyl acetate
  7. washThe combined organics were washed with saturated NaHCO3
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customPurification via flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-9b5e940c4bad477b802f093c0a7f1ffc
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07858632B2

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