p-Toluenesulfonic acid → 3-(Tetrahydro-pyran-2-yloxymethyl)-benzonitrile

HRID 1717797Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1717797
C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH:12][CH2:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[C:17]#[N:18].[O:22]1[CH:27]=[CH:26][CH2:25][CH2:24][CH2:23]1.C(=O)(O)[O-].[Na+]>ClCCl>[O:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]1[O:12][CH2:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[C:17]#[N:18]

Komponenten

6

Edukt 4

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 27346773-(Hydroxymethyl)benzonitrile

Produkt 1

HCID 219279093-(Tetrahydro-pyran-2-yloxymethyl)-benzonitrileAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Add p-toluene sulphonic acid (2.11 g, 12.2 mmol) to a solution of 3-hydroxymethyl-benzonitrile (16.30 g, 122.4 mmol) and 3,4-dihydro-2H-pyran (51.5 g, 612 mmol) in dichloromethane (500 ml) and stir. After 90 minutes, pour reaction into saturated sodium bicarbonate, remove organics, dry with sodium sulfate, filter and concentrate to give a dark brown oil. Purify the residue by flash chromatography eluting with a gradient of 10-15% ethyl acetate:hexanes to yield the title product as a clear oil (16.20 g, 61%): 1H NMR (CDCl3) δ 1.53-1.91 (m, 6H), 3.56 (m, 1H), 3.88 (m, 1H), 4.53 (d, 1H), 4.72 (t, 1H), 4.81 (d, 1H), 7.45 (t, 1H), 7.58 (m, 2H), 7.69 (s, 1H).

Aufarbeitung

  1. additionpour
  2. customremove organics
  3. dry with materialdry with sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate
  6. customto give a dark brown oil
  7. customPurify the residue by flash chromatography
  8. washeluting with a gradient of 10-15% ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-c9838b339b1f435a9ab7e5a28d4cf0f3
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07803938B2

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