Sodium amide → 5-(Benzyloxy)-1,1-dimethoxy-1,2-dihydrocyclobutabenzene

HRID 404319ノート

反応式

HRID 404319 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](Br)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16][O:17][C:18]([O:20][CH3:21])=[CH2:19].[NH2-].[Na+]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]2[CH2:19][C:18]([O:20][CH3:21])([O:17][CH3:16])[C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 24533Sodium amideHCID 136706Ketene dimethyl acetalHCID 1388351-Bromo-4-phenylmethoxybenzene

生成物 1

HCID 583801585-(Benzyloxy)-1,1-dimethoxy-1,2-dihydrocyclobutabenzene

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

To a 6 mL THF solution of 1-(benzyloxy)-4-bromobenzene (500 mg, 1900 μmol) (commercially available from Sigma-Aldrich, St. Louis, Mo., USA) and ketene dimethyl acetal (359 μL, 3800 μmol) (commercially available from Sigma-Aldrich, St. Louis, Mo., USA) was added neat sodium amide (107 μL, 3800 μmol) (commercially available from Sigma-Aldrich, St. Louis, Mo., USA). The resulting mixture was heated to 80° C. and stirred for 48 hours. After the reaction was complete, it was quenched by slow addition of water. The resulting mixture was then extracted with EtOAc. The organic layer was washed with brine and dried over MgSO4. Solvent was removed in the presence of silica gel, and the residue was purified by column chromatography with 20% EtOAc/hexane to afford desired product H7.1 (274 mg, yield, 60%). MS ESI (pos.) m/e: 271.1 (M+H)+.

後処理

  1. customit was quenched by slow addition of water
  2. extractionThe resulting mixture was then extracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. customSolvent was removed in the presence of silica gel
  6. customthe residue was purified by column chromatography with 20% EtOAc/hexane

出典と根拠

ORDレコード
ord-91aa4f8b893f40d7ac8e56fe5ed84880
出典データセット
uspto-grants-2014_06
特許番号
US08748462B2

反応ノート

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