Potassium Carbonate → HCID 86653794、化合物

HRID 85132

反応式

HRID 85132 の反応式
[Br:1][C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[CH:4]=[O:5].Cl[CH2:12][C@H:13]1[CH2:17][O:16][C:15]([CH3:19])([CH3:18])[O:14]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH2:12][C@H:13]2[CH2:17][O:16][C:15]([CH3:19])([CH3:18])[O:14]2)=[CH:6][C:3]=1[CH:4]=[O:5]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 3871792-Bromo-5-hydroxybenzaldehydeHCID 2734443(R)-(+)-4-(Chloromethyl)-2,2-dimethyl-1,3-dioxolane

生成物 1

HCID 86653794HCID 86653794、化合物収率 56%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
150 °C

実験手順

To a solution of 2-bromo-5-hydroxybenzaldehyde (62; 5 g, 0.025 mol) in DMF (100 ml) was added (R)-4-(chloromethyl)-2,2-dimethyl-1,3-dioxolane (63; 4.87 g, 0.032 mol) and K2CO3 (7.0 g, 0.05 mol). The resulting reaction mixture was stirred at 150° C. for 10 h, cooled to room temperature, diluted with water, and then extracted with EtOAc. The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. The resulting residue was purified by chromatography (petroleum ether/EtOAc=10:1 to afford the desired product, namely (S)-2-bromo-5-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)benzaldehyde 64 (4.1 g, 56%).

後処理

  1. customThe resulting reaction mixture
  2. temperaturecooled to room temperature
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by chromatography (petroleum ether/EtOAc=10:1

出典と根拠

ORDレコード
ord-7cb895ee291041ef807b9d856cc72837
出典データセット
uspto-grants-2014_09
特許番号
US08846947B2

関連ノート

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