Sodium borohydride → (E)-2-(Phenylmethylidene)deca-3,9-diyn-1-ol

HRID 1936913

Reaktionsgleichung

Reaktionsgleichung von HRID 1936913
[C:1]1(/[CH:7]=[C:8](\[C:11]#[C:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]#[CH:18])/[CH:9]=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>CO.[OH-].[Na+]>[C:1]1(/[CH:7]=[C:8](\[C:11]#[C:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]#[CH:18])/[CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 11817217(E)-2-(Phenylmethylidene)deca-3,9-diyn-1-al

Produkt 1

HCID 12022749(E)-2-(Phenylmethylidene)deca-3,9-diyn-1-olAusbeute 91,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

To a solution of Compound 2 (502 mg, 2.13 mmol) in methanol (20 mL) was added a solution of NaBH4 (80.4 mg, 2.13 mmol) in aqueous NaOH (0.5 N, 5 mL) followed by stirring at room temperature for 30 minutes. The reaction was then quenched with saturated aqueous NH4Cl (50 mL) and extracted with EtOAc (50 mL×2). The combined organic layer was washed with brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, 20 percent EtOAc in hexane) to give 462.3 mg (91.4 percent) of Compound 3: yellow oil; Rf=0.19 (17 percent EtOAc in hexane); IR (neat) 3400 (br), 3296, 2942, 2862, 2210, 2116, 1072 cm−1; 1H NMR (300 MHz, CDCl3) δ7.84-7.81 (m, 2H), 7.37-7.26 (m, 3H), 6.71 (s, 1H), 4.25 (s, 2H), 2.49 (t, J=6.65 Hz, 2H), 2.24 (td, J=6.78, 2.37 Hz, 2H), 2.17 (br s, 1H), 1.98 (t, J=2.64 Hz, 1H), 1.79-1.60 (m, 4H); 13C NMR (75 MHz, CDCl3) δ136.7, 133.3, 129.1, 128.8, 128.7, 122.5, 98.8, 84.7, 79.3, 69.3, 68.1, 28.2, 28.1, 20.0, 18.6; MS (+CI) m/z (relative intensity) 239 (M+H+, 15), 221 (100); HRMS (+EI) calcd for C17H18O 238.1358 (M+), found 238.1316.

Aufarbeitung

  1. customThe reaction was then quenched with saturated aqueous NH4Cl (50 mL)
  2. extractionextracted with EtOAc (50 mL×2)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography (silica gel, 20 percent EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-d9d4a7165cfb452ca265d55d215f9f73
Quelldatensatz
uspto-grants-2002_05
Patentnummer
US06391916B1

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