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

HRID 1883225Notes

Reaction equation

HRID 1883225 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
92 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-5e4314e55d1141bca8f5f459fdb46f7c
Source dataset
uspto-grants-2004_07
Patent number
US06759546B1

Reaction notes

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