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Ammonium Chloride → 1-[3-Phenyl-1-(toluene-4-sulfonyl)-1H-indol-2-yl]ethanol

HRID 242875
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HRID 242875 반응식
[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]([S:16]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[C:8]=2[CH:26]=[O:27])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:28][Mg]Br.[NH4+].[Cl-]>C1COCC1.C(OCC)C>[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]([S:16]([C:19]3[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=3)(=[O:17])=[O:18])[C:8]=2[CH:26]([OH:27])[CH3:28])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
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참가 물질

6

반응물 3

HCID 25517Ammonium ChlorideHCID 547518363-Phenyl-1-(toluene-4-sulfonyl)-1H-indole-2-carbaldehyde2회HCID 178418573HCID 178418573, 화합물2회

생성물 1

HCID 681570351-[3-Phenyl-1-(toluene-4-sulfonyl)-1H-indol-2-yl]ethanol

시약·촉매·용매 2

HCID 3283Diethyl Ether용매2회
HCID 8028
Tetrahydrofuran
용매

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온도
0 °C

실험 절차

To a solution of 3-phenyl-1-(toluene-4-sulfonyl)-1H-indole-2-carbaldehyde (2.11 g, 5.62 mmol) in THF (30 mL) at −78° C. and under a nitrogen atmosphere, was added 3.0M methylmagnesium bromide in diethyl ether (2.6 mL). The mixture was stirred at 0° C. for 30 min then additional 3.0M methylmagnesium bromide in diethyl ether (0.3 mL) added. After 15 min, the reaction mixture was poured into a saturated solution of NH4Cl and extracted with EtOAc (×2). The combined organic fractions were washed with water, dried (Na2SO4) and concentrated in vacuo. The crude material was combined with a second portion of crude reaction mixture obtained following the same method (starting from 140 mg, 3.73 mmol of 3-phenyl-1-(toluene-4-sulfonyl)-1H-indole-2-carbaldehyde) and the combined batches were purified by column chromatography (Si—PCC, gradient 20-100% DCM in pentane) affording the title compound as a gum which solidified on standing (2.02 g, 86%). 1H NMR (CDCl3, 400 MHz): δ 8.07 (1H, d, J=8.35), 7.80-7.75 (2H, m), 7.51-7.38 (5H, m), 7.33-7.26 (2H, m), 7.20-7.14 (3H, m), 5.25-5.15 (1H, m), 4.06 (1H, d, J=11.01 Hz), 2.31 (3H, s), 1.70 (3H, d, J=6.88 Hz)

후처리

  1. waitAfter 15 min
  2. extractionextracted with EtOAc (×2)
  3. washThe combined organic fractions were washed with water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customreaction mixture
  7. customobtained
  8. customthe combined batches were purified by column chromatography (Si—PCC, gradient 20-100% DCM in pentane)

출처 및 근거

ORD 기록
ord-2da200b888ed46b1834a2604c57dec56
출처 데이터셋
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08653089B2

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