Toluene → ethyl 2-hydroxy-2-(1-methyl-3-phenyl-1H-indol-2-yl)acetate

HRID 590954

반응식

HRID 590954 반응식
C([Li])CCC.[CH3:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:8]1.[C:22]([O:26][CH2:27][CH3:28])(=[O:25])[CH:23]=[O:24].C1(C)C=CC=CC=1>O1CCCC1>[OH:24][CH:23]([C:8]1[N:7]([CH3:6])[C:15]2[C:10]([C:9]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:22]([O:26][CH2:27][CH3:28])=[O:25]

참가 물질

6

반응물 4

HCID 1140TolueneHCID 70211Ethyl oxoacetateHCID 6101761-Methyl-3-phenylindoleHCID 178418339Butyllithium

생성물 1

HCID 70813741ethyl 2-hydroxy-2-(1-methyl-3-phenyl-1H-indol-2-yl)acetate수율 22%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of butyllithium (1.6 M, 3.44 mL, 5.5 mmol) was added at −20° C. to a solution of 1-methyl-3-phenyl-1H-indole (1b) (1.08 g, 5.3 mmol) in anhydrous tetrahydrofuran (20 mL) under a nitrogen atmosphere. After 1 hour, a solution of ethyl glyoxylate in toluene (50%, 1.1 mL, 5.5 mmol) was added. The reaction mixture was slowly warmed to room temperature for 2 hours, quenched with water (5 mL) and concentrated in vacuo. The residue was partitioned between dichloromethane (40 mL) and water (15 mL). The organic layer was washed with water (2×15 mL), brine (15 mL), dried over sodium sulfate, filtered and evaporated to dryness. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 90/10) to afford the desired alcohol (1c) as a white solid (360 mg, 1.16 mmol, 22%).

후처리

  1. customquenched with water (5 mL)
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between dichloromethane (40 mL) and water (15 mL)
  4. washThe organic layer was washed with water (2×15 mL), brine (15 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 90/10)

출처 및 근거

ORD 기록
ord-a240b766312c4329a26c1b3ed43fb300
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238026B2

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