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

HRID 38384

反応式

HRID 38384 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4fd92cd7c2664f55914ddd51d2b7f735
出典データセット
uspto-grants-2013_09
特許番号
US08524725B2

関連ノート

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