Triphenylphosphine → (S)-methyl 2-(6-((4'-((tert-butyldimethylsilyl)oxy)-2',6'-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate

HRID 2280636ノート

反応式

HRID 2280636 の反応式
[Si:1]([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][OH:23])[CH:17]=2)=[C:11]([CH3:24])[CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].O[C:26]1[CH:39]=[CH:38][C:29]2[C@H:30]([CH2:33][C:34]([O:36][CH3:37])=[O:35])[CH2:31][O:32][C:28]=2[CH:27]=1.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>[Si:1]([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][O:23][C:26]3[CH:39]=[CH:38][C:29]4[C@H:30]([CH2:33][C:34]([O:36][CH3:37])=[O:35])[CH2:31][O:32][C:28]=4[CH:27]=3)[CH:17]=2)=[C:11]([CH3:24])[CH:10]=1)([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 53393313(S)-Methyl 2-(6-hydroxy-2,3-dihydrobenzofuran-3-yl)acetateHCID 59838328(4'-((Tert-butyldimethylsilyl)oxy)-2',6'-dimethylbiphenyl-3-yl)methanol

生成物 1

HCID 89701754(S)-methyl 2-(6-((4'-((tert-butyldimethylsilyl)oxy)-2',6'-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate収率 177.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

(4′-((tert-Butyldimethylsilyl)oxy)-2′,6′-dimethylbiphenyl-3-yl)methanol 3f (1.19 g, 3.48 mmol), methyl (S)-2-(6-hydroxyl-2,3-dihydrobenzofuran-3-yl)acetate (660 mg, 3.17 mmol) and triphenylphosphine (1.34 g, 4.75 mmol) were dissolved in 10 mL of dichloromethane. The reaction solution was cooled down to 0° C., followed by addition of diisopropyl azodicarboxylate (960 mg, 4.75 mmol), then warmed up to room temperature and stirred for 4 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 (S)-methyl 2-(6-((4′-((tert-butyldimethylsilyl)oxy)-2′,6′-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate 3 g (1.28 g, yield 76.0%) as a white solid.

後処理

  1. temperaturewarmed 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-7c0a0f3085f4424f8041929b64697a31
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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