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Water → Methyl 4-[(acetyloxy)methyl]-3-methylbenzoate

HRID 501803
ノート
印刷プレビュー

反応式

HRID 501803 の反応式
[C:1]([O:4][CH2:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][C:7]=1Br)(=[O:3])[CH3:2].O.[CH2:18](OCC)C>CN(C)P(N(C)C)(N(C)C)=O.C[Sn](C)(C)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([O:4][CH2:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][C:7]=1[CH3:18])(=[O:3])[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 962WaterHCID 3283Diethyl EtherHCID 57543439Methyl 4-[(acetyloxy)methyl]-3-bromobenzoate

生成物 1

HCID 68460449Methyl 4-[(acetyloxy)methyl]-3-methylbenzoate

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 11661Tetramethyltin
溶媒
HCID 12679Hexamethylphosphoramide溶媒

反応条件

温度
70 °C

実験手順

5.30 g of methyl 4-[(acetyloxy)methyl]-3-bromobenzoate was dissolved in 50 mL of hexamethylphosphoramide, to which 6.6 mL of tetramethyltin and 0.26 g of bis(triphenylphosphine)-palladium(II) dichloride were added at room temperature in a stream of nitrogen, and this solution was stirred for 3 hours at 70° C. The reaction mixture was cooled to room temperature, and was added to a mixture of water and diethyl ether, and then the organic phase was separated therefrom. After the resultant organic phase was washed with water and a saturated sodium chloride solution, the washed phase was dried over anhydrous magnesium sulfate, and the solvent was distilled out under reduced pressure. The resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=5:1] to yield 4.17 g of methyl 4-[(acetyloxy)methyl]-3-methylbenzoate as brown oil.

後処理

  1. additionwere added at room temperature in a stream of nitrogen
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customthe organic phase was separated
  4. washAfter the resultant organic phase was washed with water
  5. dry with materiala saturated sodium chloride solution, the washed phase was dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled out under reduced pressure
  7. customThe resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=5:1]

出典と根拠

ORDレコード
ord-306d33e6cdb64af592d0789d16344254
出典データセット
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07772285B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート