ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Florhydral → 2-Ethoxy-4-(4-(3-isopropylphenyl)pent-1-enyl)phenol

HRID 718545
ノート
印刷プレビュー

反応式

HRID 718545 の反応式
[Br-].[Si]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:12][C:11]=1[O:36][CH2:37][CH3:38])(C(C)(C)C)(C)C.[Li]CCCC.[CH:44]([C:47]1[CH:48]=[C:49]([CH:53]([CH3:57])[CH2:54][CH:55]=O)[CH:50]=[CH:51][CH:52]=1)([CH3:46])[CH3:45].[N+](CCCC)(CCCC)(CCCC)CCCC.[F-]>C1COCC1.O>[CH2:37]([O:36][C:11]1[CH:12]=[C:13]([CH:16]=[CH:55][CH2:54][CH:53]([C:49]2[CH:50]=[CH:51][CH:52]=[C:47]([CH:44]([CH3:45])[CH3:46])[CH:48]=2)[CH3:57])[CH:14]=[CH:15][C:10]=1[OH:9])[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

7

反応物 4

HCID 86209FlorhydralHCID 2724141Tetrabutylammonium FluorideHCID 86702781(4-(tert-Butyldimethylsilyloxy)-3-ethoxyphenyl)methyltriphenylphosphonium bromideHCID 178418339Butyllithium

生成物 1

HCID 679819152-Ethoxy-4-(4-(3-isopropylphenyl)pent-1-enyl)phenol

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
2 回
HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
65 °C

実験手順

(4-(tert-Butyldimethylsilyloxy)-3-ethoxyphenyl)methyltriphenylphosphonium bromide (1.15 g, 1.89 mmol, 1.0 equiv.) in THF (8 mL), was cooled to 0° C. After adding n-BuLi (1.6 M in hexanes, 1.2 mL, 1.89 mmol, 1.0 equiv.) at 0° C., the red solution was stirred at 65° C. for 1 h. The mixture was re-cooled to 0° C., 3-(3-isopropylphenyl)butanal (541 mg, 2.84 mmol, 1.5 equiv.) in THF (3 mL) was added, and the mixture was stirred at 65° C. for 18 h. After addition of H2O, the aqueous layer was extracted with cyclohexane (2×), the combined organic phases were washed with brine, dried (MgSO4), filtered and the filtrate was concentrated. The residue was purified by flash chromatography on SiO2 (cyclohexane/EtOAc 98:2) to yield a colorless oil which was dissolved in THF (10 mL). n-Bu4NF (1.0 M in THF, 2.3 mL, 2.27 mmol, 1.2 equiv.) was added, and the mixture was stirred at 25° C. for 1 h. After addition of H2O, the aqueous layer was extracted with EtOAc (2×), the combined organic phases were washed with brine, dried (MgSO4), filtered and the filtrate was concentrated. The residue was purified by flash chromatography on SiO2 (cyclohexane/EtOAc 19:1→9:1) to yield 0.33 g (54% over 2 steps) of the title compound as a yellow oil.

後処理

  1. temperatureThe mixture was re-cooled to 0° C.
  2. stirringthe mixture was stirred at 65° C. for 18 h
  3. extractionthe aqueous layer was extracted with cyclohexane (2×)
  4. washthe combined organic phases were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. customThe residue was purified by flash chromatography on SiO2 (cyclohexane/EtOAc 98:2)
  9. customto yield a colorless oil which
  10. stirringthe mixture was stirred at 25° C. for 1 h
  11. extractionthe aqueous layer was extracted with EtOAc (2×)
  12. washthe combined organic phases were washed with brine
  13. dry with materialdried (MgSO4)
  14. filtrationfiltered
  15. concentrationthe filtrate was concentrated
  16. customThe residue was purified by flash chromatography on SiO2 (cyclohexane/EtOAc 19:1→9:1)

出典と根拠

ORDレコード
ord-7a79a6170ee044f08b29d97c57989b26
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

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート