Water → (R)-2-bromo-3-methyl-5-((tetrahydrofuran-3-yl)oxy)benzyl acetate

HRID 2280681ノート

反応式

HRID 2280681 の反応式
[Br:1][C:2]1[C:13]([CH3:14])=[CH:12][C:5]([O:6][C@@H:7]2[CH2:11][CH2:10][O:9][CH2:8]2)=[CH:4][C:3]=1[CH2:15]Br.[C:17]([O-:20])(=[O:19])[CH3:18].[K+].O>CN(C)C=O>[C:17]([O:20][CH2:15][C:3]1[CH:4]=[C:5]([O:6][C@@H:7]2[CH2:11][CH2:10][O:9][CH2:8]2)[CH:12]=[C:13]([CH3:14])[C:2]=1[Br:1])(=[O:19])[CH3:18]

参加物

5

反応物 3

HCID 962WaterHCID 517044Potassium AcetateHCID 117699397(R)-3-(4-bromo-3-(bromomethyl)-5-methylphenoxy)tetrahydrofuran

生成物 1

HCID 117699365(R)-2-bromo-3-methyl-5-((tetrahydrofuran-3-yl)oxy)benzyl acetate収率 99.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

(R)-3-(4-Bromo-3-(bromomethyl)-5-methylphenoxy)tetrahydrofuran 35b (700 mg, 2 mmol) was dissolved in 15 mL of N,N-dimethylformamide, followed by addition of potassium acetate (197 mg, 2 mmol). The reaction solution was heated to 50° C. and stirred for 1 hour. The resulting solution was cooled down to room temperature, mixed with 100 mL of water and extracted with ethyl acetate (20 mL×2). The combined organic extracts were washed with saturated sodium chloride solution (30 mL), dried with anhydrous magnesium sulphate, and filtered. The filtrate was concentrated under reduced pressure to obtain the crude title compound (R)-2-bromo-3-methyl-5-((tetrahydrofuran-3-yl)oxy)benzyl acetate 35c (658 mg) as a yellow oil, which was used directly in the next step without further purification.

後処理

  1. temperatureThe resulting solution was cooled down to room temperature
  2. extractionextracted with ethyl acetate (20 mL×2)
  3. washThe combined organic extracts were washed with saturated sodium chloride solution (30 mL)
  4. dry with materialdried with anhydrous magnesium sulphate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-734d119466374031853c9516b78dbeec
出典データセット
uspto-grants-2015_09
特許番号
US09139548B2

反応ノート

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