m-Chloroperbenzoic acid → 3,5-Bis-benzyloxy-4-oxiranylmethyl-benzoic acid tert-butyl ester

HRID 1643668Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1643668
[C:1]([O:5][C:6](=[O:32])[C:7]1[CH:12]=[C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:10]([CH2:21][CH:22]=[CH2:23])=[C:9]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:41])C=1>C(Cl)Cl>[C:1]([O:5][C:6](=[O:32])[C:7]1[CH:8]=[C:9]([O:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:10]([CH2:21][CH:22]2[CH2:23][O:41]2)=[C:11]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:12]=1)([CH3:2])([CH3:3])[CH3:4]

Komponenten

4

Edukt 2

HCID 70297m-Chloroperbenzoic acidHCID 595602714-Allyl-3,5-bis-benzyloxy-benzoic acid tert-butyl ester

Produkt 1

HCID 595602363,5-Bis-benzyloxy-4-oxiranylmethyl-benzoic acid tert-butyl esterAusbeute 57,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-allyl-3,5-bis-benzyloxy-benzoic acid tert-butyl ester (200d) (125 g, 0.29 mol) in CH2Cl2 was added m-CPBA (100 g, 0.58 mol) in several portions. The mixture was refluxed overnight. The solid was filtered and washed with CH2Cl2. The combined filtrates were washed with saturated aqueous Na2S2O4 (250 mL) and brine (250 mL). The organic layer was dried over Na2SO4 and concentrated to give a yellow oil. The crude oil was purified by flash column chromatography (EtOAc/petroleum ether=1/20) to give the title compound (75 g, 57.8%) as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.40 (m, 12H), 5.09(s, 4H), 3.53 (dd, 1H), 3.17 (m, 1H), 2.80 (dd, H), 2.63 (t, 1H), 2.51 (dd, 1H), 1.60 (s, 9H).

Aufarbeitung

  1. temperatureThe mixture was refluxed overnight
  2. filtrationThe solid was filtered
  3. washwashed with CH2Cl2
  4. washThe combined filtrates were washed with saturated aqueous Na2S2O4 (250 mL) and brine (250 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated
  7. customto give a yellow oil
  8. customThe crude oil was purified by flash column chromatography (EtOAc/petroleum ether=1/20)

Quellen und Nachweise

ORD-Eintrag
ord-c51190fac9d6415d97581554edfa7828
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08119624B2

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