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

HRID 220472

반응식

HRID 220472 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a89542bd527947c79ea97fb83ad6b93d
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202873B2

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