Triphenylphosphine → 5-(tetrahydro-2H-pyran-4-yloxy)indan-1-one

関与物質

役割	名称	HCID	仕込み量
反応物	Triphenylphosphine	HCID 11776	—
反応物	Tetrahydro-4H-pyran-4-ol	HCID 74956	—
反応物	5-Hydroxy-1-indanone	HCID 233147	—
反応物	Dibenzyl azodicarboxylate	HCID 5387121	—
溶媒	Tetrahydrofuran	HCID 8028	—
生成物	5-(tetrahydro-2H-pyran-4-yloxy)indan-1-one	HCID 69201344	85.1%

反応手順

5-Hydroxy-1-indanone (0.636 g, 4.30 mmol), tetrahydro-pyran-4ol (1.22 mL, 12.80 mmol), PPh3-polymer supported (2.864 g, 8.59 mmol), DBAD (1.978 g, 8.59 mmol) and THF (40 mL) were mixed, and shaken overnight. The mixture was filtered, and washed with THF (10 mL×3). The filtrate was concentrated. The residue was purified by flash chromatography to give the above intermediate (0.85 g, 85%). MS (APCI) m/z 233 (M+H)+; 1H NMR (300 MHz, CD3OD) δ ppm 1.79-1.89 (m, 2H) 2.01-2.12 (m, 2H) 2.62-2.69 (m, 2H) 3.07-3.15 (m, 2H) 3.85-4.00 (m, 4H) 4.75 (m, 1H) 6.97 (dd, J=8.65, 2.20 Hz, 1H) 7.08 (s, 1H) 7.63 (d, J=8.48 Hz, 1H).

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US07320986B2
出典データセット	uspto-grants-2008_01
ORD ID	ord-236c599371b04e038cd9929e46b28abb
出典メモ	uspto-grants-2008_01