Acetic Acid → Dimethyl (6-methyl-2-oxoheptyl)phosphonate

HRID 1386456

反応式

HRID 1386456 の反応式
[H-].[Na+].[CH3:3][O:4][P:5]([CH2:9][C:10](=[O:16])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])(=[O:8])[O:6][CH3:7].[CH2:17]1[C@@H]2OC(C[C@@H]2[C@@H](CO)[C@@H]1O)=O.C(O)(=O)C>C1COCC1>[CH3:3][O:4][P:5]([CH2:9][C:10](=[O:16])[CH2:11][CH2:12][CH2:13][CH:14]([CH3:17])[CH3:15])(=[O:8])[O:6][CH3:7]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 580181Dimethyl (2-oxoheptyl)phosphonateHCID 2724453(3aR,4S,5R,6aS)-5-Hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

生成物 1

HCID 15223968Dimethyl (6-methyl-2-oxoheptyl)phosphonate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To the suspension of sodium hydride (NaH) (60%, 250 mg) in THF (40 ml) was added dropwise dimethyl(2-oxoheptyl)phosphonate, and the reaction solution was stirred for 30 min. A THF solution (40 ml) of the aldehyde (2) previously prepared by Collins oxidization of (−)-Corey lactone (1) (2 g) was added. Reaction was maintained at room temperature overnight, and then acetic acid was added. After the usual work-up, an α,β-unsaturated ketone (3) was obtained. Yield: 1.95 g (50%).

後処理

  1. additionwas added
  2. customReaction

出典と根拠

ORDレコード
ord-e9c8e9dc483e4c37a0d75d2bdff3debb
出典データセット
uspto-grants-2001_07
特許番号
US06265440B1

関連ノート

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