Trimethylsilyl triflate → HCID 59441463, Verbindung

HRID 391162Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 391162
[OH:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:11](=[O:13])[CH3:12])[CH:8]=2)[CH2:3]1.C([Si](C)(C)O[CH:20]1[CH:25]([O:26][CH3:27])[CH:24]([O:28][CH3:29])[CH:23]([O:30][CH3:31])[CH:22]([CH3:32])[O:21]1)(C)(C)C.O([Si](C)(C)C)S(C(F)(F)F)(=O)=O>C(Cl)Cl>[CH3:27][O:26][C@@H:25]1[C@H:24]([O:28][CH3:29])[C@@H:23]([O:30][CH3:31])[C@H:22]([CH3:32])[O:21][C@H:20]1[O:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:11](=[O:13])[CH3:12])[CH:8]=2)[CH2:3]1

Komponenten

5

Edukt 3

HCID 65367Trimethylsilyl triflateHCID 59441459HCID 59441459, VerbindungHCID 68765652HCID 68765652, Verbindung

Produkt 1

HCID 59441463HCID 59441463, VerbindungAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution at 0-5° C. of 1-(2-hydroxy-indan-5-yl)-ethanone (Compound E-25; 440 mg, 2.50 mmol) and 92% w/w of tert-butyl-dimethyl-(3,4,5-trimethoxy-6-methyl-tetrahydro-pyran-2-yloxy)-silane (Compound E-23; 1.00 g, 2.87 mmol) in CH2Cl2 (6 mL) was added via syringe trimethylsilyl triflate (0.12 mL, 146 mg, 0.66 mmol). The contents were allowed to gradually warm to room temperature and were stirred overnight. The solution was diluted with CH2Cl2 and was washed once with saturated sodium bicarbonate (NaHCO3). The aqueous phase was extracted once with CH2Cl2, and the combined organics were dried (MgSO4). Concentration gave a pale green oil (783 mg, 86%): 1H NMR (CDCl3) δ 7.79 (m, 2H), 7.29 (d, J=7.6 Hz, 1H), 4.97 (s, 1H), 4.64 (m, 1H), 3.67-3.40 (m, 3H), 3.55 (s, 3H), 3.50 (s, 3H), 3.45 (s, 3H), 3.21-2.97 (m, 5H), 2.59 (s, 3H), 1.30 (d, J=6.3 Hz, H); IR (neat) 1683 cm−1.

Aufarbeitung

  1. washwas washed once with saturated sodium bicarbonate (NaHCO3)
  2. extractionThe aqueous phase was extracted once with CH2Cl2
  3. dry with materialthe combined organics were dried (MgSO4)
  4. concentrationConcentration

Quellen und Nachweise

ORD-Eintrag
ord-85334af1273449f681b7d08919b18dba
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383786B2

Notizen zur Reaktion

Wird geladen…