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Water → 4-(4-(3-Isopropylphenyl)pent-1-enyl)-1,2-dimethoxybenzene

HRID 718552
ノート
印刷プレビュー

反応式

HRID 718552 の反応式
[Br-].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH2:12][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11].[Li]CCCC.[CH:37]([C:40]1[CH:41]=[C:42]([CH:46]([CH3:50])[CH2:47][CH:48]=O)[CH:43]=[CH:44][CH:45]=1)([CH3:39])[CH3:38].O>C1COCC1>[CH:37]([C:40]1[CH:41]=[C:42]([CH:46]([CH3:50])[CH2:47][CH:48]=[CH:12][C:6]2[CH:7]=[CH:8][C:9]([O:10][CH3:11])=[C:4]([O:3][CH3:2])[CH:5]=2)[CH:43]=[CH:44][CH:45]=1)([CH3:39])[CH3:38]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 86209FlorhydralHCID 11049284(3,4-Dimethoxybenzyl)triphenylphosphonium BromideHCID 178418339Butyllithium

生成物 1

HCID 679823304-(4-(3-Isopropylphenyl)pent-1-enyl)-1,2-dimethoxybenzene収率 82.3%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒
2 回

反応条件

温度
0 °C

実験手順

A solution of (3,4-dimethoxyphenyl)methyltriphenylphosphonium bromide (4.93 g, 10.0 mmol, 1.0 equiv.) in THF (10 mL), was cooled to 0° C. After adding n-BuLi (1.6 M in hexanes, 6.3 mL, 10.0 mmol, 1.0 equiv.) at 0° C., the red suspension was stirred at 0° C. for 20 min. 3-(3-Isopropylphenyl)butanal (2.09 g, 11.0 mmol, 1.1 equiv.) in THF (11 mL) was added, and the mixture was stirred at 0° C.→25° C. for 16 h. After addition of H2O at 25° C., the aqueous layer was extracted with hexanes (2×), the combined organic phases were dried (MgSO4), filtered and the filtrate was concentrated. The residue was purified by flash chromatography on SiO2 (hexanes/EtOAc 99:1→4:1) to yield 2.67 g (82%) of the title compound as a colorless oil.

後処理

  1. stirringthe mixture was stirred at 0° C.→25° C. for 16 h
  2. extractionthe aqueous layer was extracted with hexanes (2×)
  3. dry with materialthe combined organic phases were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by flash chromatography on SiO2 (hexanes/EtOAc 99:1→4:1)

出典と根拠

ORDレコード
ord-70aa7b1a48ce4de8b2d0c96872d3c431
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09193935B2

反応ノート

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