Dichloromethane → 3-[(Tetrahydro-pyran-2-yloxy)-(4-triisopropylsilanyloxymethyl-phenyl)-methyl]-benzonitrile

HRID 1818460

Reaktionsgleichung

Reaktionsgleichung von HRID 1818460
[OH:1][CH:2]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][O:18][Si:19]([CH:26]([CH3:28])[CH3:27])([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])=[CH:13][CH:12]=1)[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7].[O:29]1[CH:34]=[CH:33][CH2:32][CH2:31][CH2:30]1.ClCCl.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(=O)([O-])O.[Na+]>[O:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH:30]1[O:1][CH:2]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][O:18][Si:19]([CH:23]([CH3:25])[CH3:24])([CH:26]([CH3:28])[CH3:27])[CH:20]([CH3:21])[CH3:22])=[CH:13][CH:12]=1)[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7]

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 666996123-[Hydroxy-(4-triisopropylsilanyloxymethyl-phenyl)-methyl]-benzonitrile

Produkt 1

HCID 574382963-[(Tetrahydro-pyran-2-yloxy)-(4-triisopropylsilanyloxymethyl-phenyl)-methyl]-benzonitrileAusbeute 100,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

Stir a solution of 3-[hydroxy-(4-triisopropylsilanyloxymethyl-phenyl)-methyl]-benzonitrile (12 g, 30.3 mmol), 3,4-dihydro-2H-pyran (3.6 mL, 39.4 mmol) and dichloromethane (250 mL) at room temperature. Add pyridinium p-toluenesulfonate (0.8 g, 3.03 mmol) and stir the resulting mixture 18 hours at room temperature. Dilute the reaction mixture with aqueous saturated sodium hydrogen carbonate (100 mL) and separate the layers. Extract the aqueous layer is washed with dichloromethane (2×50 mL), combine the organic layers, dry with magnesium sulfate, filter and concentrate. Purify the residue via silica chromatography eluting with hexanes to 8:2 hexanes:ethyl acetate to afford the title compound (14.6 g, 100%) as a colorless oil. LCMS (m/z) 478 M−1.

Aufarbeitung

  1. customseparate the layers
  2. extractionExtract the aqueous layer
  3. washis washed with dichloromethane (2×50 mL)
  4. dry with materialdry with magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify the residue via silica chromatography
  8. washeluting with hexanes to 8:2 hexanes

Quellen und Nachweise

ORD-Eintrag
ord-f51f0eba7e2540c4ab79c889e79fdd38
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07598423B2

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