Tetrakis(hydroxymethyl)phosphonium chloride → 2,2-Dimethoxyethylcyclopent-3-enol

HRID 20001Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 20001
[CH3:1][O:2][CH:3]([O:13][CH3:14])[CH2:4][C:5]([OH:12])([CH2:9][CH:10]=[CH2:11])[CH2:6]C=C.[Cl-].OC[P+](CO)(CO)CO>C(Cl)Cl.Cl[Ru](=C1N(C2C(C)=CC(C)=CC=2C)CCN1C1C(C)=CC(C)=CC=1C)(Cl)(=CC1C=CC=CC=1)[P](C1CCCCC1)(C1CCCCC1)C1CCCCC1.C(O)(C)C.[OH-].[Na+].O>[CH3:14][O:13][CH:3]([O:2][CH3:1])[CH2:4][C:5]1([OH:12])[CH2:6][CH:11]=[CH:10][CH2:9]1

Komponenten

8

Edukt 2

HCID 31298Tetrakis(hydroxymethyl)phosphonium chlorideHCID 866141134-(2,2-Dimethoxyethyl)hepta-1,6-dien-4-ol

Produkt 1

HCID 673065002,2-Dimethoxyethylcyclopent-3-enol

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 178425456HCID 178425456, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 3776IsopropanolLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

A solution of 4-(2,2-dimethoxyethyl)hepta-1,6-dien-4-ol (28 g, 140 mmol) in DCM (2L) was charged to a 3 L RB flask. Dry argon was bubbled through the solution for 30 minutes. Grubbs second generation catalyst (5.9 g, 7.0 mmol) was added and the reaction was allowed to stir under argon for 15 hours. The reaction was quenched with a solution of tetrakis-(hydroxymethyl)phosphonium chloride (27 g, 140 mmol) in isopropanol (200 mL) and 10 N NaOH (14 mL), and stirred for 15 hours. The reaction was diluted with water (1 L) and poured into a seperatory funnel. The DCM layer was separated and the aqueous was extracted with DCM (3×100 mL). The combined organics were concentrated to a dark oil which was purified by flash chromatography on a 330 g ISCO column eluting by gradient hexanes to 20% EtOAc/ hexanes over a 50 minute period. Product fractions were combined to afford the title compound.

Aufarbeitung

  1. customDry argon was bubbled through the solution for 30 minutes
  2. stirringstirred for 15 hours
  3. additionpoured into a seperatory funnel
  4. customThe DCM layer was separated
  5. extractionthe aqueous was extracted with DCM (3×100 mL)
  6. concentrationThe combined organics were concentrated to a dark oil which
  7. customwas purified by flash chromatography on a 330 g ISCO column
  8. washeluting by gradient hexanes to 20% EtOAc/ hexanes over a 50 minute period

Quellen und Nachweise

ORD-Eintrag
ord-b35f1b7b6a54453898bc9fec0b4f2792
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745484B2

Notizen zur Reaktion

Wird geladen…