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Boc-indole → tert-Butyl-1-[2-acetoxy-3-(4-octylphenoxy)propyl]indole-2-carboxylate

HRID 1821936
ノート
印刷プレビュー

反応式

HRID 1821936 の反応式
[C:1]([O:5][C:6]([C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])([CH3:4])([CH3:3])[CH3:2].BrC[CH:19]([CH2:36]C([O-])=O)[CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:24][CH:23]=1>CS(C)=O.[Na+].[Cl-]>[C:1]([O:5][C:6]([C:8]1[N:9]([CH2:36][CH:19]([O:7][C:6](=[O:5])[CH3:8])[CH2:20][O:21][C:22]2[CH:23]=[CH:24][C:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:26][CH:27]=2)[C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])([CH3:4])([CH3:2])[CH3:3]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 11458614Boc-indoleHCID 86606004HCID 86606004、化合物

生成物 1

HCID 11526497tert-Butyl-1-[2-acetoxy-3-(4-octylphenoxy)propyl]indole-2-carboxylate

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒2 回HCID 5234Sodium Chloride溶媒

反応条件

温度
110 °C

実験手順

0.325 g (1.50 mmol) tert-butylindole-2-carboxylate is dissolved in 15 ml absolute DMSO, mixed with 0.184 g (1.64 mmol) potassium-tert-butylate and stirred at 110° C. for 15 min. A solution of 0.576 g (1.50 mmol) [1-bromo-3-(4-octylphenoxy)propan-2-yl]acetate in 15 ml absolute DMSO is added drop-wise. Following 30 minutes of heating at 110° C. and subsequent cooling, hydrolysis is carried out in saturated NaCl solution. Four extractions with diethyl ether, combination of the organic phases, concentration to half the volume on the rotary evaporator, three wash steps with saturated NaCl solution, drying on sodium sulfate, filtration and reconcentration on the rotary evaporator leave as a crude product a yellow oil which is purified on silica gel by means of flash column chromatography (flow agent: petroleum ether/ethyl acetate 99:1) and yields the product as a colorless oil.

後処理

  1. waitFollowing 30 minutes
  2. temperatureof heating at 110° C.
  3. customsubsequent cooling, hydrolysis
  4. extractionFour extractions
  5. concentrationwith diethyl ether, combination of the organic phases, concentration to half the volume
  6. customon the rotary evaporator, three
  7. washwash steps with saturated NaCl solution
  8. customdrying on sodium sulfate, filtration and reconcentration on the rotary evaporator
  9. customleave as a crude product a yellow oil which
  10. customis purified on silica gel by means of flash column chromatography (flow agent: petroleum ether/ethyl acetate 99:1)

出典と根拠

ORDレコード
ord-5f644bd9e7ff4654953bc9d2d697a932
出典データセット
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07608633B2

反応ノート

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