HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 718545
Notes
Print preview

Reaction equation

HRID 718545 reaction equation
[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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
2×
HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
65 °C

Procedure

(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.

Workup

  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)

Sources & evidence

ORD record
ord-7a79a6170ee044f08b29d97c57989b26
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09193935B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes