Ethyl bromoacetate → 3-Acetyl-6-methyl-4-oxoheptanoic acid ethyl ester

HRID 220472

反応式

HRID 220472 の反応式
[CH3:1][CH:2]([CH3:10])[CH2:3][C:4](=[O:9])[CH2:5][C:6](=[O:8])[CH3:7].[H-].[Na+].[CH2:13]([O:15][C:16](=[O:19])[CH2:17]Br)[CH3:14]>O1CCCC1>[CH2:13]([O:15][C:16](=[O:19])[CH2:17][CH:5]([C:6](=[O:8])[CH3:7])[C:4](=[O:9])[CH2:3][CH:2]([CH3:10])[CH3:1])[CH3:14]

参加物

5

反応物 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 763542,4-Heptanedione, 6-methyl-

生成物 1

HCID 866416513-Acetyl-6-methyl-4-oxoheptanoic acid ethyl ester収率 73%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Add a solution of 6-methylheptane-2,4-dione (5.0 g, 35.16 mmol) in tetrahydrofuran (50 mL) dropwise to a cooled suspension (0° C.) of sodium hydride (1.69 g, 42.2 mmol, 60% dispersion in oil) in tetrahydrofuran (50 mL). After 1 hr., add bromoacetic acid ethyl ester (4.28 mL, 38.68 mmol) dropwise and stir at 0° C. to room temperature over 88 hr. Partition the reaction mixture between ethyl acetate (200 mL) and saturated aqueous ammonium chloride solution (100 mL). Separate the organic layer, dry (sodium sulfate), filter and concentrate. Purify using silica gel chromatography (95:5 hexanes:ethyl acetate) to give 3-acetyl-6-methyl-4-oxoheptanoic acid ethyl ester (5.81 g, 73%). 1H-NMR (400 MHz, CDCl3) δ 4.10 (m, 4H), 2.81 (d, 2H), 2.41 (t, 1H), 2.22 (s, 3H), 1.23 (m, 4H), 0.92 (m, 6H).

後処理

  1. customPartition the reaction mixture between ethyl acetate (200 mL) and saturated aqueous ammonium chloride solution (100 mL)
  2. customSeparate the organic layer
  3. dry with materialdry (sodium sulfate)
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify

出典と根拠

ORDレコード
ord-a89542bd527947c79ea97fb83ad6b93d
出典データセット
uspto-grants-2012_06
特許番号
US08202873B2

関連ノート

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