HCID 70165563, compound → HCID 53689601, compound

HRID 323767Notes

Reaction equation

HRID 323767 reaction equation
[CH2:1]([Zn]CC)C.[O:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[C:14](/[CH:15]=[CH:16]\[CH2:17][OH:18])[C:9]=2[CH2:8][CH2:7]1>C(Cl)Cl>[O:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[C:14]([C@H:15]3[CH2:1][C@H:16]3[CH2:17][OH:18])[C:9]=2[CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 70165563HCID 70165563, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 53689601HCID 53689601, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-15 °C

Procedure

Diethylzinc (63 mmol, 1.0 M in hexanes) was added dropwise to a mixture of (cis)-3-(2,3-dihydrobenzofuran-4-yl)prop-2-en-1-ol (12.6 mmol) in 10 mL of CH2Cl2 at −15° C. The resulting mixture was stirred at −15° C. for 1 h followed by the dropwise addition of CH2CI2 (63 mmol). The resulting mixture was warmed to RT and stirred overnight. The crude reaction mixture was then quenched with saturated aqueous NH4Cl solution at 0° and extracted with ether (2×100 mL). The combined organic extracts were washed with saturated aqueous NH4Cl solution, dried over magnesium sulfate, filtered and concentrated in vacuo. Purification by silica gel column chromatography (Hexanes:EtOAc, 4:1) provided 2.06 g (86%) of the desired product.

Workup

  1. additionfollowed by the dropwise addition of CH2CI2 (63 mmol)
  2. temperatureThe resulting mixture was warmed to RT
  3. stirringstirred overnight
  4. customThe crude reaction mixture
  5. customwas then quenched with saturated aqueous NH4Cl solution at 0°
  6. extractionextracted with ether (2×100 mL)
  7. washThe combined organic extracts were washed with saturated aqueous NH4Cl solution
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customPurification by silica gel column chromatography (Hexanes:EtOAc, 4:1)

Sources & evidence

ORD record
ord-dfdf098f535c4461ad9d27c2259f0de0
Source dataset
uspto-grants-2001_04
Patent number
US06214869B1

Reaction notes

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