Ethanol → Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate

HRID 58533

反応式

HRID 58533 の反応式
[C:1]([CH:3]1CCCC1)#[CH:2].[N+:8]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])([O-:10])=O.C([OH:19])C>C1N2CCN(CC2)C1>[OH:19][CH2:3][C:1]1[O:10][N:8]=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:2]=1

参加物

5

反応物 3

HCID 702EthanolHCID 69379Ethyl nitroacetateHCID 136725Cyclopentylacetylene

生成物 1

HCID 8027233Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate収率 96%

試薬・触媒・溶媒 1

HCID 9237Dabco触媒

反応条件

温度
80 °C

実験手順

To a mixture of ethynylcyclopentane (0.74 mL; 6.05 mmol) and ethyl 2-nitroacetate (1.37 mL; 12.11 mmol) in ethanol (9 mL) in an Ace pressure tube was added 1,4-diazobicyclo[2.2.2]octane (DABCO, 0.070 g; 0.60 mmol). The tube was heated at 80° C. for 96 h. The mixture was evaporated. The flash chromatography on silica gel (eluent: 20 to 80% dichloromethane in heptane) of the residue provided 1.21 g (96%) of ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate as an oil.

後処理

  1. customThe mixture was evaporated

出典と根拠

ORDレコード
ord-3e064e2a2ad34f739bdcb8230f179c09
出典データセット
uspto-grants-2016_09
特許番号
US09434722B2

関連ノート

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