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Sodium hydride → Z-2-Acetoxy-2-acetyl-5,9-dimethyl-deca-4,8-dienoic acid, tert-butyl ester

HRID 130374
ノート
印刷プレビュー

反応式

HRID 130374 の反応式
[C:1]([O:4][CH:5]([C:13]([CH3:15])=[O:14])[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])(=[O:3])[CH3:2].[H-].[Na+].[H][H].[CH2:20](Br)/[CH:21]=[C:22](\[CH2:24][CH2:25][CH:26]=[C:27]([CH3:29])[CH3:28])/[CH3:23]>C1COCC1>[C:1]([O:4][C:5]([C:13](=[O:14])[CH3:15])([CH2:20]/[CH:21]=[C:22](/[CH3:23])\[CH2:24][CH2:25][CH:26]=[C:27]([CH3:29])[CH3:28])[C:6]([O:8][C:9]([CH3:10])([CH3:12])[CH3:11])=[O:7])(=[O:3])[CH3:2]
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 24758Sodium hydrideHCID 6087681Neryl bromideHCID 11736056Tert-butyl 2-acetoxyacetoacetateHCID 178418361HCID 178418361、化合物

生成物 1

HCID 12046018Z-2-Acetoxy-2-acetyl-5,9-dimethyl-deca-4,8-dienoic acid, tert-butyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran
溶媒

実験手順

tert-butyl 2-acetoxyacetoacetate (B1) (19.5 g, 90 mmol) was added dropwise to a stirred suspension of NaH (2.59 g, 108 mmol) in THF (180 mL) at 0° C. After the liberation of hydrogen gas stopped, nerylbromide (19.6 g, 90 mmol) was added dropwise at 0° C. Afterwards the ice bath was removed and the mixture stirred at room temperature for 16 hours. The resulting mixture was diluted with ether (750 mL), washed with water (3 200 mL) and brine (1 200 mL), dried over Na2SO4, filtered and concentrated in vacuo. The crude product was used without further purification.

後処理

  1. customAfterwards the ice bath was removed
  2. additionThe resulting mixture was diluted with ether (750 mL)
  3. washwashed with water (3 200 mL) and brine (1 200 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was used without further purification

出典と根拠

ORDレコード
ord-9db70e5d12a8424f9c947009fcdb7fda
出典データセット
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07381743B2

反応ノート

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