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

HRID 718545
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HRID 718545 반응식
[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]
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참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962
Water
용매
2회
HCID 8028Tetrahydrofuran용매3회

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온도
65 °C

실험 절차

(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.

후처리

  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)

출처 및 근거

ORD 기록
ord-7a79a6170ee044f08b29d97c57989b26
출처 데이터셋
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09193935B2

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