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Tetrahydrofuran → (1S,5R,6R)-6-[(E)-3-Oxo-4-phenoxy-1-butenyl]-2-oxabicyclo[3,3,0]octan-3-one

HRID 1701175
ノート
印刷プレビュー

反応式

HRID 1701175 の反応式
C([C@H]1CC[C@H]2[C@@H]1CC(=O)O2)=O.O1CCCC1.[Li].[O:18]=[C:19]([CH2:40][O:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)/[CH:20]=[CH:21]/[C@H:22]1[C@H:29](OC(=O)C2C=CC=CC=2)[CH2:28][C@H:27]2[C@@H:23]1[CH2:24][C:25](=[O:39])[O:26]2>C(O)(=O)C>[O:18]=[C:19]([CH2:40][O:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)/[CH:20]=[CH:21]/[C@H:22]1[CH2:29][CH2:28][C@H:27]2[C@@H:23]1[CH2:24][C:25](=[O:39])[O:26]2
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 4

HCID 8028TetrahydrofuranHCID 3028194LithiumHCID 12767308(3aR,4R,5R,6aS)-2-oxo-4-((E)-3-oxo-4-phenoxybut-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-5-yl benzoateHCID 12884327(1S,5R,6S)-6-formyl-2-oxabicyclo[3,3,0]octan-3-one

生成物 1

HCID 22810300(1S,5R,6R)-6-[(E)-3-Oxo-4-phenoxy-1-butenyl]-2-oxabicyclo[3,3,0]octan-3-one

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A solution of 7.06 g. of (1S,5R,6S)-6-formyl-2-oxabicyclo[3,3,0]octan-3-one [E.J. Corey et al., J. Org. Chem. 39: 256 (1974)] in 450 ml. of absolute tetrahydrofuran is combined with 13.3 g. of the lithium salt of dimethyl-2-oxo-3-phenoxypropyl phosphonate (preparation: see Example 1). The mixture is stirred at room temperature under argon for 2 hours, then neutralized with glacial acetic acid, concentrated under vacuum, combined with 300 ml. of methylene chloride, and the mixture is extracted with 30 ml. of 5% sodium bicarbonate solution and then twice with respectively 30 ml. of water, dried with magnesium sulfate, and evaporated under vacuum. Recrystallization of the residue from isopropanol yields 11.0 g. (84.5% of theory) of the title compound in the form of colorless crystals.

後処理

  1. concentrationconcentrated under vacuum
  2. extractionof methylene chloride, and the mixture is extracted with 30 ml
  3. dry with materialof water, dried with magnesium sulfate
  4. customevaporated under vacuum
  5. customRecrystallization of the residue from isopropanol
  6. customyields 11.0 g

出典と根拠

ORDレコード
ord-f735cb29878546d99a5c72a4896f6852
出典データセット
uspto-grants-1980_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04191823

反応ノート

読み込み中…

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