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Hydrochloric Acid → 4-Phenethyl-benzoic acid methyl ester

HRID 2421633
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HRID 2421633 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

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

생성물 1

HCID 204665344-Phenethyl-benzoic acid methyl ester

시약·촉매·용매 2

HCID 962Water용매
HCID 8028
Tetrahydrofuran
용매

실험 절차

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).

후처리

  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%)

출처 및 근거

ORD 기록
ord-8757c6c7718340c2814ce6301b695bb3
출처 데이터셋
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07956216B2

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