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tert-Butyl acetate → tert-butyl (5S)-6-chloro-5-hydroxy-3-oxohexanoate

HRID 993419
ノート
印刷プレビュー

反応式

HRID 993419 の反応式
[H-].[Na+].[Cl-].[Mg+2].[Cl-].[C:6]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])(=[O:8])[CH3:7].[Cl:14][CH2:15][C@@H:16]([OH:23])[CH2:17][C:18](OCC)=[O:19].C([N-]C(C)C)(C)C.[Li+]>CCCCCC.O1CCCC1>[Cl:14][CH2:15][C@@H:16]([OH:23])[CH2:17][C:18](=[O:19])[CH2:7][C:6]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 10908tert-Butyl acetateHCID 24758Sodium hydrideHCID 2724682Lithium diisopropylamideHCID 5360315Magnesium ChlorideHCID 7019277Ethyl (3S)-4-chloro-3-hydroxybutanoate

生成物 1

HCID 7022053tert-butyl (5S)-6-chloro-5-hydroxy-3-oxohexanoate

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒
HCID 8058Hexane溶媒

実験手順

Separately, 240 mg (6 mmol equivalent) of sodium hydride (60% in mineral oil) was washed with hexane and, then, 6 ml of tetrahydrofuran was added. Then, at 5° C., 1.71 g (18.0 mmol) of magnesium chloride, 1.74 g (15.0 mmol) of tert-butyl acetate and 1.0 g (6 mmol) of ethyl(3S)-4-chloro-3-hydroxybutyrate were added and the mixture was stirred for 30 minutes. To this mixture, the lithium diisopropylamide solution prepared above was added dropwise over 10 minutes at the same temperature and the reaction mixture was further stirred at an elevated temperature of 25° C. for 3 hours.

後処理

  1. additionabove was added dropwise over 10 minutes at the same temperature
  2. stirringthe reaction mixture was further stirred at an elevated temperature of 25° C. for 3 hours

出典と根拠

ORDレコード
ord-a5b5c6ba3bcc418cb3707e40ce80c592
出典データセット
uspto-grants-2002_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06472544B1

反応ノート

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