methyl 2-[4-(3,4-dihydro-2H-1-benzopyran-6-yl)-2,5-dimethylthiophen-3-yl]-2-oxoacetate → methyl 2-[4-(3,4-dihydro-2H-1-benzopyran-6-yl)-2,5-dimethylthiophen-3-yl]-2-hydroxypropanoate

HRID 591067ノート

反応式

HRID 591067 の反応式
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]3[C:12]([C:18](=[O:23])[C:19]([O:21][CH3:22])=[O:20])=[C:13]([CH3:17])[S:14][C:15]=3[CH3:16])=[CH:10][C:5]=2[CH2:4][CH2:3][CH2:2]1.[CH3:24][Mg]Br>C(OCC)C>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]3[C:12]([C:18]([OH:23])([CH3:24])[C:19]([O:21][CH3:22])=[O:20])=[C:13]([CH3:17])[S:14][C:15]=3[CH3:16])=[CH:10][C:5]=2[CH2:4][CH2:3][CH2:2]1

参加物

4

反応物 2

HCID 70818547methyl 2-[4-(3,4-dihydro-2H-1-benzopyran-6-yl)-2,5-dimethylthiophen-3-yl]-2-oxoacetateHCID 178418573HCID 178418573、化合物

生成物 1

HCID 86717847methyl 2-[4-(3,4-dihydro-2H-1-benzopyran-6-yl)-2,5-dimethylthiophen-3-yl]-2-hydroxypropanoate収率 55%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
0 °C

実験手順

Under a nitrogen atmosphere, a solution of methyl 2-[4-(3,4-dihydro-2H-1-benzopyran-6-yl)-2,5-dimethylthiophen-3-yl]-2-oxoacetate (360 mg, 1.09 mmol) in anhydrous diethyl ether (5 mL) was cooled to 0° C. Methyl magnesium bromide 3.0 M in diethyl ether (0.73 mL, 2.18 mmol) was added dropwise and the reaction mixture was stirred at 0° C. for 15 minutes, before being quenched with a minimum of water. Ethyl acetate (8 mL) was added and the mixture was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100/0 to 80/20) to provide the desired alcohol (42b) (206 mg, 0.59 mmol, 55%) as a colorless oil.

後処理

  1. custombefore being quenched with a minimum of water
  2. additionEthyl acetate (8 mL) was added
  3. dry with materialthe mixture was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100/0 to 80/20)

出典と根拠

ORDレコード
ord-dffe0d7813bc4b3ab93216d4c7bbdba1
出典データセット
uspto-grants-2016_01
特許番号
US09238026B2

反応ノート

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