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m-Chloroperbenzoic acid → 5-(2,6-Dimethyl-4-triisopropylsilanyloxybenzyl)-2-methoxymethoxy-phenol

HRID 1171016
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1171016
[CH3:1][C:2]1[CH:20]=[C:19]([O:21][Si:22]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])[CH:18]=[C:17]([CH3:32])[C:3]=1[CH2:4][C:5]1[CH:6]=[CH:7][C:8]([O:13][CH2:14][O:15][CH3:16])=[C:9]([CH:12]=1)C=O.C1C=C(Cl)C=C(C(OO)=[O:41])C=1.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:32][C:17]1[CH:18]=[C:19]([O:21][Si:22]([CH:29]([CH3:31])[CH3:30])([CH:23]([CH3:25])[CH3:24])[CH:26]([CH3:27])[CH3:28])[CH:20]=[C:2]([CH3:1])[C:3]=1[CH2:4][C:5]1[CH:6]=[CH:7][C:8]([O:13][CH2:14][O:15][CH3:16])=[C:9]([OH:41])[CH:12]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 866034575-(2,6-Dimethyl-4-triisopropylsilanyloxybenzyl)-2-methoxymethoxybenzaldehyde2×

Produkt 1

HCID 666428145-(2,6-Dimethyl-4-triisopropylsilanyloxybenzyl)-2-methoxymethoxy-phenolAusbeute 42,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel
2×

Versuchsvorschrift

To 5-(2,6-dimethyl-4-triisopropylsilanyloxybenzyl)-2-methoxymethoxy-benzaldehyde (compound 15, step e; 0.460 g, 1.01 mmol) in dichloromethane 30 mL was add mCPBA (0.870 g, 2.52 mmol) and saturated sodium bicarbonate solution (2 mL). After stirring at rt overnight, the reaction mixture was poured into dichloromethane 50 mL and washed 3× with 10 mL of saturated aqueous sodium bicarbonate. The dichloromethane was dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was combined with methanol (10 mL) and 2 mL of 1 N NaOH and stirred for 1.5 hours at room temperature. The reaction was acidified with 12 N HCl (pH<3) and poured into 50 mL ethyl acetate. The layers were separated and the organics were dried over sodium sulfate, filtered and concentrated. Flash column chromatography using silica and a step gradient of hexane/ethyl acetate [20:1], hexane/ethyl acetate [9:1] provided 5-(2,6-dimethyl-4-triisopropylsilanyloxybenzyl)-2-methoxymethoxy-phenol (0.189 g, 42%): 1H NMR (300 MHz, DMSO-d6): δ 8.95 (s, 1H), 6.86 (d, 1H, J=8.1 Hz), 6.56 (s, 2H), 6.41 (d, 1H, J=2.1 Hz), 6.34 (dd, 1H, J=2.1 Hz and J=8.7 Hz), 5.05 (s, 2H), 3.78 (s, 2H), 3.38 (s, 3H), 2.13 (s, 6H), 1.11 (m, 3H), 1.00 (m, 18H); Uniplate silica gel, 250 microns; Mobile phase=10% ethyl acetate in hexane: Rf=0.15

Aufarbeitung

  1. washwashed 3× with 10 mL of saturated aqueous sodium bicarbonate
  2. dry with materialThe dichloromethane was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. stirringstirred for 1.5 hours at room temperature
  6. additionpoured into 50 mL ethyl acetate
  7. customThe layers were separated
  8. dry with materialthe organics were dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6150797ac6cd4fa89de309632b8806dc
Quelldatensatz
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07829552B2

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