Water → HCID 68107165, compound

HRID 243805Notes

Reaction equation

HRID 243805 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2(O)[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[CH3:16][Zn]C.CCCCCC.O>ClCCl.C(OCC)(=O)C.Cl.[Ti](Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH3:16])[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1

Participants

9

Reactant 4

HCID 962WaterHCID 8058HexaneHCID 59721829HCID 59721829, compoundHCID 178477796HCID 178477796, compound

Product 1

HCID 68107165HCID 68107165, compoundYield 95%

Reagents, catalysts & solvents 4

HCID 24193Titanium TetrachlorideCatalystHCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-(4-methoxyphenyl)tetrahydro-2H-pyran-4-ol (0.680 g, 3.27 mmol) in dichloromethane (16.0 mL) was cooled to −78° C., and titanium tetrachloride (0.720 mL, 6.53 mmol) was added dropwise thereto. After stirring the mixture for 1 hour, 1.0 mol/L dimethylzinc solution in n-hexane (13.1 mL, 13.1 mmol) was added dropwise thereto. The mixture was stirred for 2 hours, and water was added to stop the reaction. The temperature was returned to room temperature, and the mixture was diluted with ethyl acetate and 1 mol/L hydrochloric acid. The organic layer was washed with water and then with saturated brine, dried over anhydrous sodium sulfate and filtered. The solvent was then evaporated under reduced pressure, and the obtained residue was purified by column chromatography (silica gel, hexane/ethyl acetate=90/10-30/70) to obtain 0.641 g of the captioned compound (95% yield).

Workup

  1. stirringThe mixture was stirred for 2 hours
  2. customthe reaction
  3. customwas returned to room temperature
  4. washThe organic layer was washed with water
  5. dry with materialwith saturated brine, dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customThe solvent was then evaporated under reduced pressure
  8. customthe obtained residue was purified by column chromatography (silica gel, hexane/ethyl acetate=90/10-30/70)

Sources & evidence

ORD record
ord-37031e9a1552408a8641203b274e7da5
Source dataset
uspto-grants-2014_02
Patent number
US08653304B2

Reaction notes

Loading…