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HRID 431414作成日:2026年10月27日

Hydrochloric Acid → 3-[(Bicyclo[2.2.1]hept-5-en-2-yl)(hydroxy)methyl]oxolan-2-one

https://huagongshe.com/reaction/431414

反応式

関与物質

役割名称HCID仕込み量
反応物Hydrochloric AcidHCID 313—
反応物TetrahydrofuranHCID 8028—
反応物Bicyclo(2.2.1)hept-5-ene-2-carboxaldehydeHCID 95117—
反応物2(3H)-Furanone, 3-bromodihydro-HCID 95463—
触媒ZincHCID 23994—
溶媒HexaneHCID 8058—
生成物3-[(Bicyclo[2.2.1]hept-5-en-2-yl)(hydroxy)methyl]oxolan-2-oneHCID 1834568971.2%

反応手順

Addition reaction was carried out by mixing 98 g of zinc powder, 247 g of α-bromo-γ-butyrolactone, 122 g of 5-norbornene-2-carbaldehyde, and 2 kg of dry tetrahydrofuran and heating the mixture under reflux for 10 hours in a nitrogen atmosphere. The reaction mixture was cooled, to which dilute hydrochloric acid was added for neutralization and hexane was added for extraction. The organic layer was washed with water, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuum. Purification by silica gel column chromatography yielded 148 g (yield 71%) of α-[hydroxy(5-norbornen-2-yl)methyl]-γ-butyrolactone.

情報源と証拠

DOI10.6084/m9.figshare.5104873.v1
特許番号US06660448B2
出典データセットuspto-grants-2003_12
ORD IDord-88b6649bad3446cd9463ae695dd1dc8e
出典メモuspto-grants-2003_12