Triphenylphosphine → (R)-3-(4-bromo-3,5-dimethylphenoxy)tetrahydrofuran

HRID 2280679노트

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HRID 2280679 반응식
[O:1]1[CH2:5][CH2:4][C@H:3]([OH:6])[CH2:2]1.[Br:7][C:8]1[C:13]([CH3:14])=[CH:12][C:11](O)=[CH:10][C:9]=1[CH3:16].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>ClCCl>[Br:7][C:8]1[C:13]([CH3:14])=[CH:12][C:11]([O:6][C@@H:3]2[CH2:4][CH2:5][O:1][CH2:2]2)=[CH:10][C:9]=1[CH3:16]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 819704-Bromo-3,5-dimethylphenolHCID 2733227(S)-(+)-3-Hydroxytetrahydrofuran

생성물 1

HCID 86697120(R)-3-(4-bromo-3,5-dimethylphenoxy)tetrahydrofuran수율 73.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

(S)-Tetrahydrofuran-3-ol 2a (1 g, 11.35 mmol) was dissolved in 30 mL of dichloromethane, followed by addition of 4-bromo-3,5-dimethylphenol (2.28 g, 11.35 mmol). The reaction solution was cooled down to 0° C., followed by addition of triphenylphosphine (3.57 g, 13.62 mmol) and diisopropyl azodicarboxylate (2.75 g, 13.62 mmol) successively. The reaction solution was warmed up to room temperature and stirred for 12 hours. The resulting solution was concentrated under reduced pressure and the residue was purified by silica gel column chromatography with elution system B to obtain the title compound (R)-3-(4-bromo-3,5-dimethylphenoxy)tetrahydrofuran 35a (2.27 g, yield 73.9%) as a colorless oil.

후처리

  1. temperatureThe reaction solution was warmed up to room temperature
  2. concentrationThe resulting solution was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography with elution system B

출처 및 근거

ORD 기록
ord-602a45a7f9f145a7a017d86b2a968835
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09139548B2

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