1-Iodohexane → 5-(Hexyloxy)-2-methyl-1H-indole-3-acetic acid

HRID 484256

反応式

HRID 484256 の反応式
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH3:11])=[C:5]2[CH2:12][C:13]([OH:15])=[O:14].C[O-].[Na+].[CH2:19](I)[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>CO>[CH2:19]([O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH3:11])=[C:5]2[CH2:12][C:13]([OH:15])=[O:14])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

参加物

5

反応物 3

HCID 125271-IodohexaneHCID 10942334Sodium MethoxideHCID 11310252O-Desmethyl-N-deschlorobenzoyl Indomethacin

生成物 1

HCID 199357575-(Hexyloxy)-2-methyl-1H-indole-3-acetic acid収率 62%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 5-hydroxy-2-methyl-1H-indole-3-acetic acid (7.17 g, 35.0 mmol) in methanol (40 mL) is added sodium methoxide (70 mmol). The solution is evaporated, dimethylformamide (40 mL) is added followed by hexyl iodide (35.0 mmol). After 2 days the solvent is removed and the residue is partitioned between ethyl acetate and pH=4 buffer. The organic layer is separated, dried over MgSO4 and evaporated to 8.6 g of a brown solid. Recrystallization from ethanol/water affords 6.23 g (62%) of white crystals, m.p. 65°-67° C.

後処理

  1. customThe solution is evaporated
  2. additiondimethylformamide (40 mL) is added
  3. customAfter 2 days the solvent is removed
  4. customthe residue is partitioned between ethyl acetate and pH=4 buffer
  5. customThe organic layer is separated
  6. dry with materialdried over MgSO4
  7. customevaporated to 8.6 g of a brown solid
  8. customRecrystallization from ethanol/water

出典と根拠

ORDレコード
ord-1e2dbac9c99d4930a37317edb68511d2
出典データセット
uspto-grants-1993_07
特許番号
US05229516

関連ノート

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