Carbon Dioxide → 1-(Tol-4-yl)3,4-dihydro-4,4-dimethyl-7-naphthaldehyde

関与物質

役割	名称	HCID	仕込み量
反応物	Carbon Dioxide	HCID 280	—
反応物	Dimethylformamide	HCID 6228	—
反応物	Pentane	HCID 8003	—
反応物	6-Bromo-1,1-dimethyl-4-p-tolyl-1,2-dihydronaphthalene	HCID 10687622	—
反応物	HCID 178418306	HCID 178418306	—
溶媒	Tetrahydrofuran	HCID 8028	—
溶媒	Ethyl Acetate	HCID 8857	—
生成物	1-(Tol-4-yl)3,4-dihydro-4,4-dimethyl-7-naphthaldehyde	HCID 86588677	—

反応手順

To a cold (-78° C.), stirred solution of 1-(tol-4-yl)3,4-dihydro-4,4-dimethyl-7-bromo-naphthalene (Compound B 1 g, 3.2 mmol), in THF (17 mL) was added t-BuLi in pentane (1.7M solution, 3 mL, 5.1 mmol). After 10 minutes dry dimethylformamide (DMF) (600 mg, 8 mmol) was added and the dry-ice cooling was replaced with ice-water bath. The mixture was gradually warmed to ambient temperature and diluted with ethylacetate (150 mL), washed with water (15 mL). The organic layer was dried with MgSO4 and solvent was removed under reduced pressure. The crude material was purified by silicagel chromatography to afford the title compound as a white solid.

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US05728846
出典データセット	uspto-grants-1998_03
ORD ID	ord-bf0cea00f0c14b87bedbeafd627d9061
出典メモ	uspto-grants-1998_03