Benzyl Bromide → 2-[3,4-Dimethoxy-2-phenylmethylphenyl]-4,5-dihydro-4,4-dimethyloxazole

HRID 1381605Notes

Reaction equation

HRID 1381605 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[O:12][CH2:13][C:14]([CH3:17])([CH3:16])[N:15]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C([Li])CCC.[C:23]1([CH2:29]Br)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O1CCCC1>[CH3:1][O:2][C:3]1[C:4]([CH2:29][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:5]([C:11]2[O:12][CH2:13][C:14]([CH3:17])([CH3:16])[N:15]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 27791682-(3,4-Dimethoxyphenyl)-4,4-dimethyl-2-oxazolineHCID 178418339Butyllithium

Product 1

HCID 212762762-[3,4-Dimethoxy-2-phenylmethylphenyl]-4,5-dihydro-4,4-dimethyloxazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-[3,4-Dimethoxyphenyl]-4,5-dihydro 4,4-dimethyloxazole (15 g) in dry tetrahydrofuran (100 ml) under a nitrogen atmosphere was cooled to -45° in a chlorobenzene/dry ice bath. Butyl lithium (45.9 ml 1.6M solution) was added dropwise and the mixture stirred at -45° for 2 hours. Phenylmethyl bromide (38 ml) was then added dropwise and the mixture allowed to stir at 20° for 16 hours. The mixture was quenched with brine and the aqueous phase extracted with ether. The organic phase was separated, dried over magnesium sulphate, filtered and evaporated to leave a solid. Purification by flash chromatography (30% ether/40/60 petrol) gave the title compound as a colourless solid (10.58 g); mp 81°-82°.

Workup

  1. stirringto stir at 20° for 16 hours
  2. customThe mixture was quenched with brine
  3. extractionthe aqueous phase extracted with ether
  4. customThe organic phase was separated
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. customto leave a solid
  9. customPurification by flash chromatography (30% ether/40/60 petrol)

Sources & evidence

ORD record
ord-ff4d587b4fb94e08a4126cbf8cdd766b
Source dataset
uspto-grants-1989_02
Patent number
US04803225

Reaction notes

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