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

HRID 502875ノート

反応式

HRID 502875 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-cd5345cf22f84f82b7a580e1d860095d
出典データセット
uspto-grants-2010_08
特許番号
US07776882B2

反応ノート

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