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Tetrahydrofuran → 2-(3-Fluoro-2-methyl-benzyl)-7-methoxycarbonyl-1-phenyl-indolizine-3-carboxylic acid

HRID 1963055
ノート
印刷プレビュー

反応式

HRID 1963055 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][N:8]2[C:12]([CH:13]=1)=[C:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:10]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:22]=1[CH3:28])=[C:9]2[CH:29]=[O:30])=[O:4].P([O-])(O)(O)=[O:32].[Na+].CC(=CC)C.C1COCC1.Cl([O-])=O.[Na+]>C(O)(C)(C)C.O.[Cl-].[Na+].O.CC(=O)OCC>[F:27][C:23]1[C:22]([CH3:28])=[C:21]([CH:26]=[CH:25][CH:24]=1)[CH2:20][C:10]1[C:11]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[C:12]2[N:8]([C:9]=1[C:29]([OH:32])=[O:30])[CH:7]=[CH:6][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:13]2
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

10

反応物 5

HCID 8028Tetrahydrofuran2 回HCID 105532-Methyl-2-butene2 回HCID 23668197Sodium Chlorite2 回HCID 23672064Monosodium phosphate2 回HCID 88414465Methyl-2-(3-fluoro-2-methyl-benzyl)-3-formyl-1-phenyl-indolizine-7-carboxylate

生成物 1

HCID 67773634
2-(3-Fluoro-2-methyl-benzyl)-7-methoxycarbonyl-1-phenyl-indolizine-3-carboxylic acid
収率 137.8%

試薬・触媒・溶媒 4

HCID 962Water溶媒2 回HCID 6386tert-Butanol溶媒HCID 8857Ethyl Acetate溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
0 °C

実験手順

The compound of step 3 (0.293 g, 0.73 mmol) was suspended in 4 ml of tert-butanol and cooled to 0° C. To this suspension were added a solution of sodium dihydrogenphosphate (0.263 g, 2.19 mmol) in 1 ml of water, a 2 M solution of 2-methyl-2-butene in THF (2.19 ml, 4.38 mmol) and sodium chlorite (0.124 g, 1.09 mmol) in small portions. After stirring at room temperature for 18 h, once more a solution of sodium dihydrogenphosphate (0.263 g, 2.19 mmol) in 2 ml water, a 2 M solution of 2-methyl-2-butene in THF (2.19 ml, 4.38 mmol) and sodium chlorite (0.124 g, 1.09 mmol) were added again and stirring was continued for an additional 48 h. Then 30 ml of a 1:1 mixture of brine and EA were added, the organic phase was separated, and the aqueous phase was extracted with EA. The combined organic phases were washed with brine, dried over sodium sulfate, filtered and evaporated to dryness under reduced pressure to give 0.420 g of the crude title compound as a yellow powder which was directly used in the next step.

後処理

  1. stirringstirring
  2. waitwas continued for an additional 48 h
  3. additionwere added
  4. customthe organic phase was separated
  5. extractionthe aqueous phase was extracted with EA
  6. washThe combined organic phases were washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated to dryness under reduced pressure

出典と根拠

ORDレコード
ord-643d0edd8be345d5b361a10ea6d4241e
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08415336B2

反応ノート

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