Diethyl Ether → HCID 18381637, compound

HRID 2297410Notes

Reaction equation

HRID 2297410 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][CH2:11][C:12]([CH3:15])([CH3:14])[N:13]=2)=[CH:5][CH:4]=1.[CH2:16]([Li])[CH2:17][CH2:18][CH3:19].C([O:23][CH2:24][CH3:25])C>CCCCCC>[CH3:14][C:12]1([CH3:15])[CH2:11][O:10][C:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][C:7]=2[CH:24]([OH:23])[CH2:25][CH2:19][CH2:18][CH2:17][C:16]2[CH:7]=[CH:8][CH:3]=[CH:4][CH:5]=2)=[N:13]1

Participants

5

Reactant 3

HCID 3283Diethyl Ether2×HCID 3593374,5-Dihydro-2-(4-methoxyphenyl)-4,4-dimethyloxazoleHCID 178418339Butyllithium

Product 1

HCID 18381637HCID 18381637, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A solution of 2-(4-methoxy-phenyl)-4,4-dimethyl-4,5-dihydro-oxazole (1.85 g, 9 mmoles), prepared as described in example 1, in dry ethyl ether (37 ml), at 0° C. was added with 2.5M n-butyl lithium (4 ml, 9.9 mmoles) in hexane, keeping the temperature below 5° C. The mixture was left at 0° C. for 4 hours, then dropwise added with a solution of 5-phenyl-pentanale (3.25 g, 20 mmoles) in dry ethyl ether (10 ml), keeping the temperature below 5° C. The mixture was kept at room temperature for 2 days, then poured into water/ice. The phases were separated and the aqueous one was extracted again with ethyl ether. The organic ones were discoloured with charcoal, anhydrified and concentrated to give an oil which was purified by flash chromatography (eluent: petrolatum/ethyl acetate 8:2, then 7:3) to give 1.17 g of the title compound (yield: 35%).

Workup

  1. customthe temperature below 5° C
  2. customthe temperature below 5° C
  3. waitThe mixture was kept at room temperature for 2 days
  4. customThe phases were separated
  5. extractionthe aqueous one was extracted again with ethyl ether
  6. concentrationconcentrated
  7. customto give an oil which
  8. customwas purified by flash chromatography (eluent

Sources & evidence

ORD record
ord-ed85f6b3cd9e4ae6bbddde6c59f21a7c
Source dataset
uspto-grants-2002_12
Patent number
US06492360B1

Reaction notes

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