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

HRID 1613486ノート

反応式

HRID 1613486 の反応式
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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 8028Tetrahydrofuran溶媒

実験手順

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%.

後処理

  1. customthe product purified

出典と根拠

ORDレコード
ord-d8017a71e47548479823ac197ed7242b
出典データセット
uspto-grants-1993_03
特許番号
US05192800

反応ノート

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