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

HRID 590967

반응식

HRID 590967 반응식
C([Li])CCC.[C:6]1([N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:21]([O:25][CH2:26][CH3:27])(=[O:24])[CH:22]=[O:23].C1(C)C=CC=CC=1>O1CCCC1>[OH:23][CH:22]([C:13]1[N:12]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:20]2[C:15]([CH:14]=1)=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:21]([O:25][CH2:26][CH3:27])=[O:24]

참가 물질

6

반응물 4

HCID 1140TolueneHCID 70211Ethyl oxoacetateHCID 1820291-Phenyl-1H-indoleHCID 178418339Butyllithium

생성물 1

HCID 70813712ethyl 2-hydroxy-2-(1-phenyl-1H-indol-2-yl)acetate수율 19%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of butyllithium (1.6 M, 1.19 mL, 1.9 mmol) was added at −78° C. to a solution of 1-phenyl-1H-indole (5a) (350 mg, 1.81 mmol) in tetrahydrofuran (10 mL) under a nitrogen atmosphere. After 45 minutes, a solution of ethyl glyoxylate in toluene (50%, 400 μL, 2 mmol) was added. The reaction mixture was slowly warmed to room temperature for 12 hours, quenched with water (2 mL) and concentrated in vacuo. The residue was partitioned between dichloromethane (30 mL) and water (10 mL). The organic layer was washed with water (2×10 mL), brine (10 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 (5b) as a white solid (100 mg, 0.33 mmol, 19%).

후처리

  1. customquenched with water (2 mL)
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between dichloromethane (30 mL) and water (10 mL)
  4. washThe organic layer was washed with water (2×10 mL), brine (10 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-e651d3765b184ad7b428914d243b832a
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238026B2

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