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Hydrochloric Acid → 4-Phenethyl-benzoic acid methyl ester

HRID 2421633
ノート
印刷プレビュー

反応式

HRID 2421633 の反応式
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7](OS(C(F)(F)F)(=O)=O)=[CH:6][CH:5]=1.CN1CCCC1=O.[CH2:26]([Mg]Br)[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.Cl>O.C1COCC1>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:6][CH:5]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 13387N-methyl-2-pyrrolidoneHCID 5315090Methyl 4-(((trifluoromethyl)sulfonyl)oxy)benzoateHCID 178419670HCID 178419670、化合物

生成物 1

HCID 204665344-Phenethyl-benzoic acid methyl ester

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 8028
Tetrahydrofuran
溶媒

実験手順

76A (2.27 g, 8 mmol), N-methylpyrrolidinone (4.4 mL), Fe(acac)3 (140 mg, 0.4 mmol) and dry THF (50 mL) were stirred under nitrogen at room temperature. Phenethylmagnesium bromide (1.0 M in THF, 10 mL) was added by syringe. After stirring for fifteen minutes, HCl (1 M, 20 mL) was slowly added. The mixture was diluted with water and extracted three times with EtOAc. The organic layers were combined, washed with water and then brine, were dried over MgSO4 and were concentrated. Purification was achieved using flash chromatography on SiO2 with hexanes/toluene 50:50. A colourless oil was obtained (1.575 g, 82%). NMR 1H (ppm, CDCl3): 7.94 (d, J3 8.2 Hz, 2H), 7.29-7.13 (m, 7H), 3.89 (s, 3H), 3.01-2.89 (m, 4H).

後処理

  1. extractionextracted three times with EtOAc
  2. washwashed with water
  3. dry with materialbrine, were dried over MgSO4
  4. concentrationwere concentrated
  5. customPurification
  6. customA colourless oil was obtained (1.575 g, 82%)

出典と根拠

ORDレコード
ord-8757c6c7718340c2814ce6301b695bb3
出典データセット
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07956216B2

反応ノート

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