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Diethyl Ether → ethyl 5-{(2RS,3RS)-3-amino-2-(4-nitrophenyl)butyl}-2-furancarboxylate

HRID 581040
ノート
印刷プレビュー

反応式

HRID 581040 の反応式
[N:1]([CH:4]([CH3:26])[CH:5]([C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1)[CH2:6][C:7]1[O:11][C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9][CH:8]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)C>O1CCCC1.O>[NH2:1][CH:4]([CH3:26])[CH:5]([C:17]1[CH:18]=[CH:19][C:20]([N+:23]([O-:25])=[O:24])=[CH:21][CH:22]=1)[CH2:6][C:7]1[O:11][C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9][CH:8]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 3283Diethyl EtherHCID 11776TriphenylphosphineHCID 54125754ethyl 5-{(2RS,3RS)-3-azido-2-(4-nitrophenyl)butyl}-2-furancarboxylate

生成物 1

HCID 53734556ethyl 5-{(2RS,3RS)-3-amino-2-(4-nitrophenyl)butyl}-2-furancarboxylate収率 96.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回
HCID 8028
Tetrahydrofuran
溶媒

実験手順

3.24 g of ethyl 5-{(2RS,3RS)-3-azido-2-(4-nitrophenyl)butyl}-2-furancarboxylate was dissolved in a mixed solution of 50 ml of tetrahydrofuran and 5 ml of water, and 2.37 g of triphenylphosphine was added thereto, followed by heating and refluxing for 6 hours. The reaction solution was left to cool to room temperature, and then ethyl ether and water were added thereto for extraction. The organic layer was washed with a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The drying agent was filtered off, and then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/methanol=100/1+20/1) to obtain 2.89 g of the above-identified compound.

後処理

  1. additionwas added
  2. temperatureby heating
  3. temperaturerefluxing for 6 hours
  4. waitThe reaction solution was left
  5. extractionfor extraction
  6. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationThe drying agent was filtered off
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (methylene chloride/methanol=100/1+20/1)

出典と根拠

ORDレコード
ord-9f33cc1b1a0d4ef5b4402c31df59d396
出典データセット
uspto-grants-1999_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05919786

反応ノート

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