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

HRID 2280679ノート

反応式

HRID 2280679 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-602a45a7f9f145a7a017d86b2a968835
出典データセット
uspto-grants-2015_09
特許番号
US09139548B2

反応ノート

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