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

HRID 1883225ノート

反応式

HRID 1883225 の反応式
[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]

参加物

7

反応物 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 121440122-Propoxy-3,5-diisopropyl-phenylboronic acid2 回HCID 570811153-Iodopent-2-en-1-ol

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒

反応条件

温度
92 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-5e4314e55d1141bca8f5f459fdb46f7c
出典データセット
uspto-grants-2004_07
特許番号
US06759546B1

反応ノート

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