Sodium Carbonate → HCID 59032962、化合物

HRID 40632

反応式

HRID 40632 の反応式
[CH3:1][C:2]1[NH:3][C:4]2[CH:5]=[CH:6][CH:7]=[C:8]([OH:11])[C:9]=2[CH:10]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH2:22](OS(C1C=CC=C([N+]([O-])=O)C=1)(=O)=O)[C@@H:23]1[O:25][CH2:24]1.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C.C1COCC1>[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[C:8]([O:11][CH2:22][C@@H:23]1[CH2:24][O:25]1)[CH:7]=[CH:6][CH:5]=2

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 146513Benzenesulfonic acid, 3-nitro-, (2R)-2-oxiranylmethyl esterHCID 5902254-Hydroxy-2-methylindoleHCID 2724254Sodium bis(trimethylsilyl)amide

生成物 1

HCID 59032962HCID 59032962、化合物

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

2-Methyl-1H-indol-4-ol (0.58 g, 3.9 mmol) and THF (20 mL) were placed in a round bottom flask and stirred at room temperature. Sodium bis(trimethylsilyl) amide (3.9 mL, [1M] in THF) was then slowly added to the reaction mixture. After fifteen minutes of stirring at room temperature (R)-glycidyl-3-nitrobenzenesulfonate was added and the reaction mixture was allowed to stir overnight. Work up of the reaction mixture was carried out with saturated sodium carbonate solution and ethyl acetate. The organic layer was dried with sodium sulfate, filtered and the solvent was removed under reduced pressure to yield a crude oil. The crude oil was purified by flash chromatography (20% Ethyl acetate/heptane) to yield the title compound as a crystalline solid.

後処理

  1. additionwas added
  2. stirringto stir overnight
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customto yield a crude oil
  7. customThe crude oil was purified by flash chromatography (20% Ethyl acetate/heptane)

出典と根拠

ORDレコード
ord-ebd93b289be04dc6a4baa50243d59af2
出典データセット
uspto-grants-2013_09
特許番号
US08530475B2

関連ノート

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