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

HRID 1501958

반응식

HRID 1501958 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

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:

후처리

  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)

출처 및 근거

ORD 기록
ord-287c85a584e84c2bb447152dd826e36e
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206199B2

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