Toluene → 3-(3,5-Diisopropyl-2-propoxy-phenyl)-pent-2-en-1-ol

HRID 1883225노트

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HRID 1883225 반응식
[CH2:1]([O:4][C:5]1[C:10]([CH:11]([CH3:13])[CH3:12])=[CH:9][C:8]([CH:14]([CH3:16])[CH3:15])=[CH:7][C:6]=1B(O)O)[CH2:2][CH3:3].I[C:21]([CH2:25]C)=[CH:22]CO.[C:27]([O-:30])([O-])=O.[Na+].[Na+].[C:33]1(C)C=CC=CC=1>CCO.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>[CH:21]([C:6]1[C:5]([O:4][CH2:1][CH2:2][CH3:3])=[C:10]([C:11]([CH2:13][CH3:33])=[CH:12][CH2:27][OH:30])[CH:9]=[C:8]([CH:14]([CH3:16])[CH3:15])[CH:7]=1)([CH3:25])[CH3:22]

참가 물질

7

반응물 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 121440122-Propoxy-3,5-diisopropyl-phenylboronic acid2회HCID 570811153-Iodopent-2-en-1-ol

생성물 1

HCID 698645863-(3,5-Diisopropyl-2-propoxy-phenyl)-pent-2-en-1-ol수율 56%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매

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온도
92 °C

실험 절차

A mixture of 2-propoxy-3,5-diisopropyl-phenylboronic acid (Intermediate 4, 3.28 g, 12.4 mmol), 3-iodo-pent-2-en-1-ol (3.95 g, 18.6 mmol), Pd(PPh3)4 (720 mg, 0.62 mmol), and Na2CO3 (2M, 31 mL, 62 mmol) in toluene (40 mL) and EtOH (30 mL) was heated to 92° C. for overnight. The reaction was cooled to room temperature and extracted with EtOAc (×3). The organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The additional 1.10 g of Intermediate 4 as described above was subjected to the same reaction conditions to also give crude product. The combined crude products were purified by flash column chromatography on silica gel (10% EtOAc-hexanes) to yield the title compound as a light brown oil (9.2 g, 56% over 2 steps).

후처리

  1. temperatureThe reaction was cooled to room temperature
  2. extractionextracted with EtOAc (×3)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customabove was subjected to the same reaction conditions
  7. customto also give crude product
  8. customwere purified by flash column chromatography on silica gel (10% EtOAc-hexanes)

출처 및 근거

ORD 기록
ord-5e4314e55d1141bca8f5f459fdb46f7c
출처 데이터셋
uspto-grants-2004_07
특허 번호
US06759546B1

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