Allyl bromide → 4-Benzyl-3-(2-cyclohexyl-pent-4-enoyl)-oxazolidin-2-one

HRID 502875노트

반응식

HRID 502875 반응식
[CH2:1]([CH:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:22])[CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH2:33](Br)[CH:34]=[CH2:35]>O1CCCC1>[CH2:1]([CH:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:22])[CH:15]([CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1)[CH2:35][CH:34]=[CH2:33])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 7841Allyl bromideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 186863194-Benzyl-3-(2-cyclohexyl-acetyl)-oxazolidin-2-one

생성물 1

HCID 574757124-Benzyl-3-(2-cyclohexyl-pent-4-enoyl)-oxazolidin-2-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 4-benzyl-3-(2-cyclohexyl-acetyl)-oxazolidin-2-one (16.0 g, 53 mmol) in anhydrous tetrahydrofuran at −78° C. was added a 1.0 M solution of sodium bis(trimethylsilyl)-amide (79.0 mL, 79 mmol), and the reaction mixture was stirred for 1 h. To the reaction mixture was then added allyl bromide (18.4 mL, 213 mmol), and the temperature was raised to −45° C. The reaction mixture was stirred at this temperature for 3 h. The reaction was quenched with aqueous saturated NH4Cl solution, and the resulting mixture was warmed to room temperature. The reaction mixture was extracted with ethyl acetate, and the combined extracts were washed with brine. The organic layers were dried (MgSO4) and concentrated in vacuo to yield a residue that was purified by silica gel column chromatography (5:1 hexanes:ethyl acetate) to yield (4-benzyl-3-(2-cyclohexyl-pent-4-enoyl)-oxazolidin-2-one) as a thick liquid that became a solid upon storage.

후처리

  1. stirringThe reaction mixture was stirred at this temperature for 3 h
  2. customThe reaction was quenched with aqueous saturated NH4Cl solution
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. washthe combined extracts were washed with brine
  5. dry with materialThe organic layers were dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto yield a residue that
  8. customwas purified by silica gel column chromatography (5:1 hexanes:ethyl acetate)

출처 및 근거

ORD 기록
ord-cd5345cf22f84f82b7a580e1d860095d
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776882B2

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