Tetrabutylammonium Fluoride → 3-[(4-Hydroxymethyl-phenyl)-(tetrahydro-pyran-2-yloxy)-methyl]-benzonitrile

HRID 1818461

Reaktionsgleichung

Reaktionsgleichung von HRID 1818461
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[O:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]1[O:25][CH:26]([C:35]1[CH:40]=[CH:39][C:38]([CH2:41][O:42][Si](C(C)C)(C(C)C)C(C)C)=[CH:37][CH:36]=1)[C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=1)[C:30]#[N:31]>O1CCCC1.O>[OH:42][CH2:41][C:38]1[CH:39]=[CH:40][C:35]([CH:26]([O:25][CH:20]2[CH2:21][CH2:22][CH2:23][CH2:24][O:19]2)[C:27]2[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=2)[C:30]#[N:31])=[CH:36][CH:37]=1

Komponenten

5

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 574382963-[(Tetrahydro-pyran-2-yloxy)-(4-triisopropylsilanyloxymethyl-phenyl)-methyl]-benzonitrile

Produkt 1

HCID 574382993-[(4-Hydroxymethyl-phenyl)-(tetrahydro-pyran-2-yloxy)-methyl]-benzonitrileAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

Add a 1M solution in tetrahydrofuran of tetrabutylammonium fluoride (37 mL, 37 mmol) to a solution of 3-[(tetrahydro-pyran-2-yloxy)-(4-triisopropylsilanyloxymethyl-phenyl)-methyl]-benzonitrile (14.6 g, 30.4 mmol) in tetrahydrofuran (50 mL) and tetrahydrofuran stir at room temperature for 2 hours. Concentrate the reaction, dilute with water (200 mL), and extract with ethyl acetate (2×100 mL). Combine the extracts, dry over magnesium sulfate, filter, and concentrate. Purify the residue via silica chromatography eluting with 9:1 hexanes:ethyl acetate to 1:1 hexanes ethyl acetate to afford the title compound (8.0 g, 82%), as a colorless thick oil. LCMS (m/z) 323 M+1.

Aufarbeitung

  1. concentrationConcentrate
  2. customthe reaction
  3. extractionextract with ethyl acetate (2×100 mL)
  4. dry with materialCombine the extracts, dry over magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify the residue via silica chromatography
  8. washeluting with 9:1 hexanes

Quellen und Nachweise

ORD-Eintrag
ord-54f038a4ff5a49228e742ce1afa7ed1e
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07598423B2

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