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

HRID 1381605ノート

反応式

HRID 1381605 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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°.

後処理

  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)

出典と根拠

ORDレコード
ord-ff4d587b4fb94e08a4126cbf8cdd766b
出典データセット
uspto-grants-1989_02
特許番号
US04803225

反応ノート

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