Iodoethane → methyl 2-(4-chlorophenyl)-2-(4-formyl-1H-indol-1-yl)butanoate

HRID 1427258노트

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HRID 1427258 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:13]2[C:21]3[C:16](=[C:17]([CH:22]=[O:23])[CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14]2)[C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.I[CH2:35][CH3:36]>C1COCC1.CN(P(N(C)C)(N(C)C)=O)C.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([N:13]2[C:21]3[C:16](=[C:17]([CH:22]=[O:23])[CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14]2)([CH2:35][CH3:36])[C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:7]=1

참가 물질

7

반응물 3

HCID 6340IodoethaneHCID 2733832Lithium HexamethyldisilazideHCID 86705047methyl 2-(4-chlorophenyl)-2-(4-formyl-1H-indol-1-yl)acetate

생성물 1

HCID 86705048methyl 2-(4-chlorophenyl)-2-(4-formyl-1H-indol-1-yl)butanoate

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매HCID 12679Hexamethylphosphoramide용매

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온도
0 °C

실험 절차

To a solution of methyl 2-(4-chlorophenyl)-2-(4-formyl-1H-indol-1-yl)acetate (2.34 g, 7.17 mmol) in THF (60 mL) and HMPA (15 mL) was added LiHMDS (1 M in THF, 11.0 mL, 11 mmol) dropwise at 0° C. The mixture was stirred at 0° C. for 30 min before adding iodoethane (1.23 g, 7.88 mmol). After stirring for another 30 min at 0° C., the mixture was diluted with EtOAc (120 mL) and then quenched with water (20 mL). The organic layer was separated and washed with brine (20 mL), dried over Na2SO4, filtered and the solvent was removed in vacuo. The residue was purified via column chromatography (0-15% EtOAc/hexanes) to provide the title compound.

후처리

  1. stirringAfter stirring for another 30 min at 0° C.
  2. customquenched with water (20 mL)
  3. customThe organic layer was separated
  4. washwashed with brine (20 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent was removed in vacuo
  8. customThe residue was purified via column chromatography (0-15% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-509438ede45e4a1db05f0be18bd4973a
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933113B2

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