HCID 10856043, compound → HCID 11063306, compound

HRID 368778Notes

Reaction equation

HRID 368778 reaction equation
[CH3:1][Al](C)C.[O:5]1[C@@H:9]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C@@H:6]1[CH2:7][OH:8]>Cl>[OH:5][C@H:6]([C@H:9]([CH3:1])[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:7][OH:8]

Participants

4

Reactant 2

HCID 10856043HCID 10856043, compoundHCID 16682925Trimethylaluminum

Product 1

HCID 11063306HCID 11063306, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

To a 5 L 3-neck round-bottom flask equipped with a mechanical stirrer, thermocouple and nitrogen inlet was added a mixture of hexanes (IL). The vessel was cooled to 0° C. A 2.0M solution of Me3Al in hexanes (800 mL, 1.6 mol) was added, followed by a solution of epoxide 16 (120 g, 0.677 mol) in hexanes (250 mL)/CH12C12 (50 mL), maintaining the temperature below 20° C. Upon complete addition, the cloudy reaction mixture was stirred at 5° C. for 35 min. Then a solution of 10% HCl (300 mL) was added dropwise, followed by the addition of conc HCl (350 mL). The layers were separated, and the organic phase was washed with brine and dried over MgSO4. After removal of the volatiles in vacuo, the title compound (122.1 g) was obtained as an oil.

Workup

  1. customTo a 5 L 3-neck round-bottom flask equipped with a mechanical stirrer
  2. additionthermocouple and nitrogen inlet was added
  3. temperaturemaintaining the temperature below 20° C
  4. additionUpon complete addition
  5. customthe cloudy reaction mixture
  6. customThe layers were separated
  7. washthe organic phase was washed with brine
  8. dry with materialdried over MgSO4
  9. customAfter removal of the volatiles in vacuo

Sources & evidence

ORD record
ord-358769f8418a4b15bf3f312005f71c93
Source dataset
uspto-grants-2000_10
Patent number
US06133457

Reaction notes

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