Triphenylphosphine → (2R)-2-[(5-Methoxy-2-nitrophenoxy)methyl]oxirane

HRID 270128

反応式

HRID 270128 の反応式
[O:1]1[CH2:3][C@@H:2]1[CH2:4][OH:5].[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([N+:15]([O-:17])=[O:16])=[C:12](O)[CH:13]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([N+:15]([O-:17])=[O:16])=[C:10]([CH:9]=1)[O:5][CH2:4][C@H:2]1[CH2:3][O:1]1

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 2196355-Methoxy-2-nitrophenolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 6973630(-)-Glycidol

生成物 1

HCID 86601492(2R)-2-[(5-Methoxy-2-nitrophenoxy)methyl]oxirane収率 72.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a mixture of (2S)-oxiran-2-ylmethanol (296.3 mg, 4.0 mmol), 5-methoxy-2-nitrophenol (676.6 mg, 4.0 mmol) and triphenyl phosphine (1.05 g, 4.0 mmol) in THF (10 mL) was added diethyl azodicarboxylate (DEAD, 704.6 mg, 4.0 mmol) in THF (5 mL) dropwise at room temperature. After addition was completed the reaction mixture was stirred at room temperature overnight. The volatiles were removed in vacuo and the residue was purified by silica gel flash chromatography (040% ethyl acetate in petroleum spirit) to give the subtitled compound (650 mg).

後処理

  1. additionAfter addition
  2. customThe volatiles were removed in vacuo
  3. customthe residue was purified by silica gel flash chromatography (040% ethyl acetate in petroleum spirit)

出典と根拠

ORDレコード
ord-a161776fb2e24e1792f765b9ca986115
出典データセット
uspto-grants-2008_11
特許番号
US07449475B2

関連ノート

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