Dimethylformamide → HCID 10805854、化合物

HRID 1069652ノート

反応式

HRID 1069652 の反応式
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[NH:8][CH:7]=1)[CH3:2].CN(C=O)C.[H-].[Na+].[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1COCC1.O.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:7]=1)[CH3:2]

参加物

8

反応物 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 105138025-Methoxy-1H-indole-3-acetic acid ethyl ester

生成物 1

HCID 10805854HCID 10805854、化合物収率 82%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

5-Methoxy-1H-indole-3-acetic acid ethyl ester (10.1 g, 41 mmol) was dissolved in 50 mL of THF and 200 mL of DMF and 1.8 g (45 mmol) of 60% NaH/mineral oil were added in portions with cooling. After 0.17 hours, 5 mL (42 mmol) of benzyl bromide was added and stirring maintained for 1.5 hours. The mixture was diluted with water and ethyl acetate, the organic layer separated, washed with water, brine and dried (Na2SO4). The solution was evaporated at reduced pressure and the residue chromatographed on silica gel eluting with a gradient, 25% ethyl acetate/hexane→40% ethyl acetate/hexane, to give 10.8 g (82% yield) of 5-methoxy-1-(phenylmethyl)-1H-indole-3-acetic acid ethyl ester.

後処理

  1. temperaturewith cooling
  2. temperaturemaintained for 1.5 hours
  3. customthe organic layer separated
  4. washwashed with water, brine
  5. dry with materialdried (Na2SO4)
  6. customThe solution was evaporated at reduced pressure
  7. customthe residue chromatographed on silica gel eluting with a gradient, 25% ethyl acetate/hexane→40% ethyl acetate/hexane

出典と根拠

ORDレコード
ord-568b0a439dba470d8a06677c45589ceb
出典データセット
uspto-grants-2001_06
特許番号
US06252084B1

反応ノート

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