Tert-butyl 2-(bromomethyl)prop-2-enoate → 3-(1-Carboxycyclopentyl)-2-methylenepropanoic acid t-butyl ester

HRID 1086720Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1086720
C(OC(=O)C(CCOC)C[C:12]1([C:17]([OH:19])=[O:18])[CH2:16][CH2:15][CH2:14][CH2:13]1)C1C=CC=CC=1.Br[CH2:26][C:27](=[CH2:35])[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29]>O1CCCC1.[Cl-].[Zn+2].[Cl-]>[C:31]([O:30][C:28](=[O:29])[C:27](=[CH2:35])[CH2:26][C:12]1([C:17]([OH:19])=[O:18])[CH2:16][CH2:15][CH2:14][CH2:13]1)([CH3:34])([CH3:33])[CH3:32]

Komponenten

5

Edukt 2

HCID 10955115Tert-butyl 2-(bromomethyl)prop-2-enoateHCID 146221281-{2-[(Benzyloxy)carbonyl]-4-methoxybutyl}-cyclopentanecarboxylic acid

Produkt 1

HCID 540038933-(1-Carboxycyclopentyl)-2-methylenepropanoic acid t-butyl esterAusbeute 259,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Cyclopentane carboxylic acid dilithio dianion (prepared from cyclopentane carboxylic acid (2.58 g) as described in Example 15) in tetrahydrofuran (100 ml) was treated with zinc chloride (1.85 g) at room temperature for 30 minutes, followed by t-butyl 2-bromomethylpropenoate (5.0 g) at -78° C. The reaction mixture was worked-up and the product purified as previously described to give 3-(1-carboxycyclopentyl)-2-methylenepropanoic acid t-butyl ester as an oil (5.1 g, 89%). Found: C,66.16; H,8.89. C14H22O4 requires C,66.11; H,8.72%.

Aufarbeitung

  1. customthe product purified

Quellen und Nachweise

ORD-Eintrag
ord-f1f304705cfa4300b3d0d3a942afb3db
Quelldatensatz
uspto-grants-1991_07
Patentnummer
US05030654

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