Ammonium Chloride → Ethanone, 1-(4-chloro-3-fluorophenyl)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-

HRID 2279450ノート

反応式

HRID 2279450 の反応式
[Si:1]([O:8][CH2:9][C:10](N(OC)C)=[O:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([Mg]Br)=[CH:19][C:18]=1[F:25].[NH4+].[Cl-]>C1COCC1>[Si:1]([O:8][CH2:9][C:10]([C:20]1[CH:21]=[CH:22][C:17]([Cl:16])=[C:18]([F:25])[CH:19]=1)=[O:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 116010942-(tert-butyldimethylsilyloxy)-N-methoxy-N-methylacetamideHCID 178505943HCID 178505943、化合物

生成物 1

HCID 68294408Ethanone, 1-(4-chloro-3-fluorophenyl)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-収率 93.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of 60 (15.12 g, 64.79 mmol) and THF (50 mL) cooled to 0° C. was added dropwise (4-chloro-3-fluorophenyl)magnesium bromide (226.8 mL, 113.4 mmol) and the solution was stirred at 0° C. for 2 h. Saturated NH4Cl was added and the reaction was extracted with DCM. The organic layer was separated, dried, filtered and concentrated. The crude product was purified by passage through a SiO2 plug eluting with 5% EtOAc/hexane to afford 18.36 g (93.6%) of 2-(tert-butyldimethylsilyloxy)-1-(4-chloro-3-fluorophenyl)ethanone (62).

後処理

  1. extractionthe reaction was extracted with DCM
  2. customThe organic layer was separated
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by passage through a SiO2 plug
  7. washeluting with 5% EtOAc/hexane

出典と根拠

ORDレコード
ord-d5290904d5624326901fbd297282c949
出典データセット
uspto-grants-2015_09
特許番号
US09133187B2

反応ノート

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