Water → HCID 19838848, compound

HRID 2165209Notes

Reaction equation

HRID 2165209 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10]Br)[CH:6]=[CH:7][CH:8]=1.[Mg].[CH3:13][C:14]1([CH3:31])[CH2:18][O:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[C:20]=2OC)=[N:15]1.O>O1CCCC1>[CH3:28][O:27][C:21]1[C:20]([CH2:10][CH2:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)=[C:19]([C:16]2[O:17][CH2:18][C:14]([CH3:13])([CH3:31])[N:15]=2)[CH:24]=[CH:23][C:22]=1[O:25][CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 1374501-Bromo-2-(3-methoxyphenyl)ethaneHCID 5462224MagnesiumHCID 110217964,5-Dihydro 4,4-dimethyl-2-(2,3,4-trimethoxyphenyl)oxazole

Product 1

HCID 19838848HCID 19838848, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 2-(3-methoxyphenyl)ethylbromide (12.2 g) in dry tetrahydrofuran (20 ml) was added dropwise to a suspension of magnesium (1.46 g) in dry tetrahydrofuran (20 ml), under an atmosphere of nitrogen, at a rate sufficient to maintain a state of reflux. After 1 hour the cooled solution was added to a stirred solution of 4,5-dihydro-4,4-dimethyl-2-(2,3,4-trimethoxyphenyl) oxazole (7.95 g) in dry tetrahydrofuran (50 ml) under an atmosphere of nitrogen. The mixture was stirred at 20° for 16 hours. Water (400 ml) was added and the aqueous phase thoroughly extracted with ethyl acetate (2×250 ml). The organic phase was dried over magnesium sulphate, filtered and the solvent removed in vacuo to yield a yellow oil which was purified by flash column chromatography on silica gel, using 10% ethyl acetate/90% petroleum ether as eluent, and by Kugelruhr distillation (air bath temperature 200°/1 mm Hg) 9.7 g of the title compound were obtained ms m/e 369.

Workup

  1. temperatureto maintain a state
  2. temperatureof reflux
  3. extractionthe aqueous phase thoroughly extracted with ethyl acetate (2×250 ml)
  4. dry with materialThe organic phase was dried over magnesium sulphate
  5. filtrationfiltered
  6. customthe solvent removed in vacuo
  7. customto yield a yellow oil which
  8. customwas purified by flash column chromatography on silica gel
  9. distillationby Kugelruhr distillation (air bath temperature 200°/1 mm Hg) 9.7 g of the title compound
  10. customwere obtained ms m/e 369

Sources & evidence

ORD record
ord-e591fc7a91444da797755d4cda49926a
Source dataset
uspto-grants-1990_07
Patent number
US04939147

Reaction notes

Loading…