StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Water → Racemic 2-allylcyclopropyl acetate

HRID 60541
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 60541
[CH2:1]([CH:4]1[CH2:8][CH2:7][CH2:6][CH:5]1[OH:9])C=C.C(N(CC)CC)C.[C:17](Cl)(=[O:19])[CH3:18].O>CC1OCCC1>[C:17]([O:9][CH:5]1[CH2:6][CH:7]1[CH2:8][CH:4]=[CH2:1])(=[O:19])[CH3:18]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 124762962-(Prop-2-en-1-yl)cyclopentan-1-ol

Produkt 1

HCID 118159957Racemic 2-allylcyclopropyl acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 73012-MethyltetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Into a reaction vessel was added 2-allylcyclopentanol M (1 equivalent) in MeTHF (10 volumes). The vessel was purged with nitrogen and the solution was then cooled to 0° C. Triethylamine (3.0 equivalents) was then slowly added to the solution over about 30 minutes. The mixture was allowed to stir for about 30 minutes after which acetyl chloride (2.5 equivalents) was added maintaining the internal temperature about below 20° C. The reaction was then allowed to stir for at least 12 hours at about 21° C. After the allotted time, water (6 volumes) was slowly charged to the reactor and the phases were separated. The organic layer was then washed with 2M hydrochloric acid (6 volumes), 10 wt. % sodium bicarbonate (6 volumes) and then brine (6 volumes). The organic layer is concentrated under reduced pressure at about 0° C. to obtain crude racemic 2-allylcyclopropyl acetate N. 1H NMR (400 MHz, CDCl3): δ 5.85-5.73 (m, 1H), 5.10-5.04 (m, 1H), 5.00-4.97 (m, 1H), 3.85-3.82 (m, 1H), 2.13-2.07 (m, 1H), 1.99 (s, 3H), 2.01-1.89 (m, 1H), 1.14-1.03 (m, 1H), 0.87-0.76 (m, 1H), 0.64-0.57 (m, 1H).

Aufarbeitung

  1. customThe vessel was purged with nitrogen
  2. additionwas added
  3. temperaturemaintaining the internal temperature about below 20° C
  4. customthe phases were separated
  5. washThe organic layer was then washed with 2M hydrochloric acid (6 volumes), 10 wt. % sodium bicarbonate (6 volumes)
  6. concentrationThe organic layer is concentrated under reduced pressure at about 0° C.

Quellen und Nachweise

ORD-Eintrag
ord-31239966a7754f9088a2dda60d0ee047
Quelldatensatz
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09440991B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion