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

HRID 270128

반응식

HRID 270128 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-a161776fb2e24e1792f765b9ca986115
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449475B2

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