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

HRID 1613486노트

반응식

HRID 1613486 반응식
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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 8028Tetrahydrofuran용매

실험 절차

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%.

후처리

  1. customthe product purified

출처 및 근거

ORD 기록
ord-d8017a71e47548479823ac197ed7242b
출처 데이터셋
uspto-grants-1993_03
특허 번호
US05192800

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