Methyl Acrylate → methyl (2E,5R)-6-(benzyloxy)-5-(2,2-diethoxyethoxy)hex-2-enoate

HRID 538026

Reaktionsgleichung

Reaktionsgleichung von HRID 538026
[CH2:1]([O:3][CH:4]([O:20][CH2:21][CH3:22])[CH2:5][O:6][C@H:7]([CH2:17][CH:18]=[CH2:19])[CH2:8][O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:2].[C:23]([O:27][CH3:28])(=[O:26])C=C>ClCCl.CC1C=C(C)C(N2C(=[Ru](Cl)(Cl)=CC3C=CC=CC=3)N(C3C(C)=CC(C)=CC=3C)CC2)=C(C)C=1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1>[CH2:10]([O:9][CH2:8][C@H:7]([O:6][CH2:5][CH:4]([O:3][CH2:1][CH3:2])[O:20][CH2:21][CH3:22])[CH2:17]/[CH:18]=[CH:19]/[C:23]([O:27][CH3:28])=[O:26])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

5

Edukt 2

HCID 7294Methyl AcrylateHCID 59281174[(R)-2-(2,2-diethoxyethoxy)-4-pentenyloxymethyl]benzene

Produkt 1

HCID 86729528methyl (2E,5R)-6-(benzyloxy)-5-(2,2-diethoxyethoxy)hex-2-enoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11147261(1,3-Dimesitylimidazolidin-2-ylidene)(tricyclohexylphosphine)benzylidene ruthenium dichlorideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

This reaction was carried out in 10 batches. To a solution of C2 (10 g, 32 mmol) in dichloromethane (400 mL) was added [1,3-bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(phenylmethylene)(tricyclohexylphosphine)ruthenium (Grubbs 2nd-generation catalyst, 1.38 g, 1.62 mmol) and methyl prop-2-enoate (69.7 g, 0.81 mol), and the reaction mixture was stirred at room temperature for 18 hours. Solvent was removed in vacuo, and the residue was purified via silica gel chromatography (Eluent: 3:1 petroleum ether/ethyl acetate) to provide the product as a yellow oil. Combined yield: 70 g, 0.19 mol, 59%. 1H NMR (400 MHz, CDCl3) δ 7.27-7.38 (m, 5H), 6.94-7.04 (m, 1H), 5.89 (br d, J=15.6 Hz, 1H), 4.58 (dd, J=5.3, 5.0 Hz, 1H), 4.54 (s, 2H), 3.73 (s, 3H), 3.44-3.7 (m, 9H), 2.41-2.55 (m, 2H), 1.21 (t, J=7.0 Hz, 3H), 1.20 (t, J=7.0 Hz, 3H).

Aufarbeitung

  1. customSolvent was removed in vacuo
  2. customthe residue was purified via silica gel chromatography (Eluent: 3:1 petroleum ether/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-c9dcf23af0394fac92a90f9daae75d61
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08865706B2

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