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

HRID 37707

반응식

HRID 37707 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2918c717de254b449985b0c368a94450
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05420289

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