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Triethylamine → 6-(4-Hydroxymethyl-2-methoxy-5-nitrophenoxy)hexyl acetate

HRID 987394
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 987394
[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[C:15]([CH:21]=[O:22])=[CH:14][C:13]=1[O:23][CH3:24])(=[O:3])[CH3:2].[BH4-].[Na+].[Cl-].[NH4+].C(N(CC)CC)C>C(O)C.ClCCl>[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[C:15]([CH2:21][OH:22])=[CH:14][C:13]=1[O:23][CH3:24])(=[O:3])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 180087936-(4-Formyl-2-methoxy-5-nitrophenoxy)hexyl acetate

Produkt 1

HCID 180087906-(4-Hydroxymethyl-2-methoxy-5-nitrophenoxy)hexyl acetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702
Ethanol
Lösungsmittel
HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A flame-dried, 250 mL round bottom flask was charged, under argon, with 4 (8 g, 23.6 mmol) and this was suspended in 35 mL of anhydrous ethanol. The flask was protected from light and then placed in an ice bath. Sodium borohydride (2.06 g, 54.3 mmol) was added in small portions and the reaction was allowed to stir at 0° C. for 180 minutes. At this time, saturated ammonium chloride (30 mL) was added slowly to the reaction mixture over a period of 20 minutes to minimize the gas evolution. Ethanol was evaporated in vacuo and the mixture was diluted with water (100 ml) and extracted with dichloromethane (3×100 mL). The combined organic layers were dried with magnesium sulfate, filtered, and the solvent was evaporated in vacuo to give orange oil. This oil was subjected to column chromatography (SiO2, 75×200 mm, 1% triethylamine in dichloromethane) to give, following solvent evaporation, 7.25 g (90%) of 5 as a yellow solid. Rf=0.30 (33% ethyl acetate/hexane). Mp >220° C. 1H NMR (400 MHz, DMSO-d6): δ7.67 (s, 1), 7.38 (s, 1), 5.55 (t, J=6.4 Hz, 1), 4.81 (d, J=6.4 Hz, 2), 4.04 (t, J=7.2 Hz, 2), 4.00 (t, J=7.6 Hz, 2), 3.91 (s, 3), 1.99 (s, 3), 1.76-1.72 (m, 2), 1.61-1.57 (m, 2), 1.45-1.37 (m, 4) ppm.

Aufarbeitung

  1. customplaced in an ice bath
  2. customEthanol was evaporated in vacuo
  3. additionthe mixture was diluted with water (100 ml)
  4. extractionextracted with dichloromethane (3×100 mL)
  5. dry with materialThe combined organic layers were dried with magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent was evaporated in vacuo
  8. customto give orange oil
  9. customto give
  10. customsolvent evaporation, 7.25 g (90%) of 5 as a yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-fa3fd1c378ed4818ab6545cb6c6e043c
Quelldatensatz
uspto-grants-2003_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06632641B1

Notizen zur Reaktion

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