Trifluoromethanesulfonic anhydride → 8-Methyl-2-phenylchroman-7-yl trifluoromethanesulfonate

HRID 1811021Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1811021
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[CH3:16][C:17]1[C:18](O)=[CH:19][CH:20]=[C:21]2[C:26]=1[O:25][CH:24]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:23][CH2:22]2>C(Cl)Cl.N1C=CC=CC=1.CCOC(C)=O>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][C:18]1[C:17]([CH3:16])=[C:26]2[C:21]([CH2:22][CH2:23][CH:24]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[O:25]2)=[CH:20][CH:19]=1)(=[O:5])=[O:4]

Komponenten

6

Edukt 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 142248968-Methyl-2-phenylchroman-7-ol

Produkt 1

HCID 593750168-Methyl-2-phenylchroman-7-yl trifluoromethanesulfonateAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Step 2 Trifluoromethanesulfonic anhydride (0.613 mL, 3.63 mmol) was added dropwise to a solution of 8-methyl-2-phenylchroman-7-ol (671 mg, 2.79 mmol) in DCM (10 mL) and pyridine (10 mL) at 0° C. After 30 min, the mixture was diluted with EtOAc (70 mL), washed with water (2×30 mL) and brine (30 mL), dried and concentrated. The residue was purified by column chromatography (eluting with a gradient from 95:5 to 85:15 hexane-EtOAc) to give 8-methyl-2-phenylchroman-7-yl trifluoromethanesulfonate as colorless liquid (925 mg, 89%). 1H NMR (400 MHz, chloroform-d) δ 7.28-7.61 (5 H, m), 6.97 (1 H, d, J=8.58 Hz), 6.79 (1 H, d, J=8.58 Hz), 5.11 (1 H, dd, J=10.23, 2.31 Hz), 2.99 (1 H, ddd, J=16.73, 11.11, 5.83 Hz), 2.68-2.88 (1 H, m), 2.17-2.32 (4 H, m), 1.88-2.12 (1 H, m). Mass spectrum m/z 390.0 (M+H)+.

Aufarbeitung

  1. washwashed with water (2×30 mL) and brine (30 mL)
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography (
  5. washeluting with a gradient from 95:5 to 85:15 hexane-EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-19f48af94e0f445ca3f01124d53e5904
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362065B2

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