2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → (3R)-3-methyl-6-(prop-1-en-2-yl)-3,4-dihydro-1H-isochromen-1-one

HRID 1501958

反応式

HRID 1501958 の反応式
[C:1]([Mg]Br)([CH3:3])=[CH2:2].Br[C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[O:12][C@H:11]([CH3:18])[CH2:10]2.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>C1COCC1.[Cl-].[Zn+2].[Cl-]>[CH3:18][C@@H:11]1[CH2:10][C:9]2[C:14](=[CH:15][CH:16]=[C:7]([C:1]([CH3:3])=[CH2:2])[CH:8]=2)[C:13](=[O:17])[O:12]1

参加物

6

反応物 3

HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 71270763(3R)-6-bromo-3-methyl-3,4-dihydro-1H-isochromen-1-oneHCID 178456138HCID 178456138、化合物

生成物 1

HCID 89619009(3R)-3-methyl-6-(prop-1-en-2-yl)-3,4-dihydro-1H-isochromen-1-one

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

A 0.5 molar solution of zinc chloride (1.696 g, 12.44 mmol) in dry THF (16.59 mL) was cooled to 0° C. A solution of isopropenylmagnesium bromide (24.89 mL, 12.44 mmol) was added via syringe. The reaction was stirred at 0° C. for 30 minutes before being cannulated into a sealed tube containing (3R)-6-bromo-3-methyl-3,4-dihydro-1H-isochromen-1-one (2.00 g, 8.30 mmol), PdOAc2 (0.093 g, 0.42 mmol), and X—PHOS (0.395 g, 0.830 mmol) in THF (16.6 mL) under N2 atmosphere. The tube was heated to 70° C. overnight. The reaction was then cooled and partitioned between water (100 mL) and EtOAc (220 mL). The organic layer was then washed with brine, dried over magnesium sulfate, filtered and concentrated. MPLC purification (10-50% EtOac/Hex) gave (3R)-3-methyl-6-(prop-1-en-2-yl)-3,4-dihydro-1H-isochromen-1-one:

後処理

  1. custombefore being cannulated into a sealed tube
  2. temperatureThe tube was heated to 70° C. overnight
  3. temperatureThe reaction was then cooled
  4. custompartitioned between water (100 mL) and EtOAc (220 mL)
  5. washThe organic layer was then washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customMPLC purification (10-50% EtOac/Hex)

出典と根拠

ORDレコード
ord-287c85a584e84c2bb447152dd826e36e
出典データセット
uspto-grants-2015_12
特許番号
US09206199B2

関連ノート

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