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

HRID 1427258ノート

反応式

HRID 1427258 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒HCID 12679Hexamethylphosphoramide溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-509438ede45e4a1db05f0be18bd4973a
出典データセット
uspto-grants-2015_01
特許番号
US08933113B2

反応ノート

読み込み中…