Triphenylphosphine → 4-(4-Bromo-3,5-dimethylphenoxy)thiane

HRID 15625

반응식

HRID 15625 반응식
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:10].[S:11]1[CH2:16][CH2:15][CH:14](O)[CH2:13][CH2:12]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][CH:14]2[CH2:15][CH2:16][S:11][CH2:12][CH2:13]2)=[CH:4][C:3]=1[CH3:10]

참가 물질

6

반응물 4

HCID 11776Triphenylphosphine2회HCID 819704-Bromo-3,5-dimethylphenolHCID 220568ethyl N-ethoxycarbonyliminocarbamate2회HCID 576296Tetrahydro-2H-thiopyran-4-ol2회

생성물 1

HCID 593425534-(4-Bromo-3,5-dimethylphenoxy)thiane수율 86.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 4-bromo-3,5-dimethylphenol (0.201 g, 1.00 mmol), tetrahydro-2H-thiopyran-4-ol (0.130 g, 1.10 mmol) and triphenylphosphine (0.341 g, 1.30 mmol) in tetrahydrofuran (5 mL) was added diethyl azodicarboxylate (40% solution in toluene, 0.591 mL, 1.30 mmol), and the mixture was stirred at room temperature for 1.5 hr. Tetrahydro-2H-thiopyran-4-ol (0.0591 g, 0.500 mmol), triphenylphosphine (0.157 g, 0.600 mmol) and diethyl azodicarboxylate (40% solution in toluene, 0.272 mL, 0.600 mmol) were added, and the mixture was further stirred for 1.5 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-20:80) to give the title compound (0.261 g, yield 86%) as colorless crystals.

후처리

  1. stirringthe mixture was further stirred for 1.5 hr
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-20:80)

출처 및 근거

ORD 기록
ord-f048dd03d4064e58a82769102e031e02
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732626B2

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