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

HRID 1613486Notes

Reaction equation

HRID 1613486 reaction equation
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]

Participants

5

Reactant 2

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

Product 1

HCID 540038933-(1-Carboxycyclopentyl)-2-methylenepropanoic acid t-butyl esterYield 259.9%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

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%.

Workup

  1. customthe product purified

Sources & evidence

ORD record
ord-d8017a71e47548479823ac197ed7242b
Source dataset
uspto-grants-1993_03
Patent number
US05192800

Reaction notes

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