Benzyl Chloride → 1-Benzyl-2-phenyl-1H-indole

HRID 5595

반응식

HRID 5595 반응식
[C:1]1([C:7]2[NH:8][C:9]3[C:14]([CH:15]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:16](Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[OH-].[K+]>O.C1(C)C=CC=CC=1>[CH2:16]([N:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:15]=[C:7]1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

참가 물질

6

반응물 3

HCID 7503Benzyl ChlorideHCID 136982-PhenylindoleHCID 14797Potassium Hydroxide

생성물 1

HCID 117480441-Benzyl-2-phenyl-1H-indole수율 13.2%

시약·촉매·용매 2

HCID 962Water용매2회HCID 1140Toluene용매

실험 절차

A mixture of 19.33 g (0.1 mole) of 2-phenylindole, 13.92 g (0.11 mole) of benzyl chloride, 33 g (0.5 mole) of 85% KOH, 14 mL of H2O, 2.5 g (2.5 mmoles) of PEG-1000, and 100 mL of toluene was stirred and heated at 55°-60° for 24 hours. After cooling to room temperature, 100 mL of H2O was added. The layers were separated. The aqueous layer was extracted with 100 mL of toluene. The combined toluene phases were washed with 2N HCl (2×50 mL), H2O (2×50 mL), and 50 mL of brine and dried over MgSO4. Evaporation of the solvent left 32.3 g of dark brown oil. The oil was chromatographed on a 1100 g column of silica gel. The column was elut4d with 25% CH2Cl2 -Skellysolve B and 200 mL fractions were collected. The fractions were assayed by silica gel tlc (1×4") (25% CH2Cl2 -Skellysolve B). Fractions 18-20 were combined giving 3.74 g (13%) of 1-benzyl-2-phenylindole as a solid.

후처리

  1. temperatureheated at 55°-60° for 24 hours
  2. customThe layers were separated
  3. extractionThe aqueous layer was extracted with 100 mL of toluene
  4. washThe combined toluene phases were washed with 2N HCl (2×50 mL), H2O (2×50 mL), and 50 mL of brine
  5. dry with materialdried over MgSO4
  6. customEvaporation of the solvent
  7. waitleft 32.3 g of dark brown oil
  8. customThe oil was chromatographed on a 1100 g column of silica gel
  9. customwere collected

출처 및 근거

ORD 기록
ord-3ef121dbf1f0400b85825dd9302cc9ce
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05245046

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