Triphenylphosphine → ethyl-(2E)-3-methyl-5-[(1-phenyl-1-H-tetrazol-5-yl)thio]pent-2-enoate

HRID 1363844ノート

反応式

HRID 1363844 の反応式
[SH:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[N:4][N:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[CH2:46]([O:48][C:49](=[O:56])/[CH:50]=[C:51](\[CH3:55])/[CH2:52][CH2:53]O)[CH3:47]>C(OCC)(=O)C.C1COCC1>[CH2:46]([O:48][C:49](=[O:56])/[CH:50]=[C:51](\[CH3:55])/[CH2:52][CH2:53][S:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[N:4][N:3]=1)[CH3:47]

参加物

7

反応物 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 59865204ethyl-(2E)-5-hydroxy-3-methylpent-2-enoateHCID 1785279861-phenyltetrazole-5-thiol

生成物 1

HCID 59516418ethyl-(2E)-3-methyl-5-[(1-phenyl-1-H-tetrazol-5-yl)thio]pent-2-enoate収率 98.2%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

This reaction was performed with reference to the literature (Mitsunobu, O., Synthesis, 1981, 1-28.). 5-Mercapto-1-phenyltetrazole (16.30 g, 91.20 mmol), triphenylphosphine (27.30 g, 104 mmol) and diisopropyl azodicarboxylate (95%, 21.10 g, 104 mmol) were added to a THF (410 ml) solution of ethyl-(2E)-5-hydroxy-3-methylpent-2-enoate (13.80 g, 86.90 mmol) while ice cooling. The reaction solution was warmed to room temperature and stirred for four hours. After the reaction solution was diluted with ethyl acetate, it was washed with distilled water and brine. After the organic layer was dried over anhydrous sodium sulfate and the drying agent was filtered off, the organic layer was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (Merck, commercial name Silica Gel 60, 230-400 mesh; hexane:ethyl acetate=5:1) to obtain the title compound (27.16 g) as a white solid.

後処理

  1. custom, Synthesis, 1981, 1-28
  2. washwas washed with distilled water and brine
  3. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate
  4. filtrationthe drying agent was filtered off
  5. concentrationthe organic layer was concentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (Merck, commercial name Silica Gel 60, 230-400 mesh; hexane:ethyl acetate=5:1)

出典と根拠

ORDレコード
ord-a2e97dc0cc4e4011b8205dbfbc639a5d
出典データセット
uspto-grants-2011_02
特許番号
US07884128B2

反応ノート

読み込み中…