Potassium Carbonate → [(2R)-7-(Methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-YL]methanol

참여 물질

역할	이름	HCID	투입량
반응물	Potassium Carbonate	HCID 11430	—
반응물	L-Proline	HCID 145742	—
반응물	Sodium methanesulfinate	HCID 2733271	—
반응물	(R)-(7-Bromo-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol	HCID 66879096	—
촉매	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
용매	Dimethyl Sulfoxide	HCID 679	—
생성물	[(2R)-7-(Methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-YL]methanol	HCID 66878426	78.2%

반응 단계

Two batches of [(2R)-7-bromo-2,3-dihydro-1,4-benzodioxin-2-yl]methanol (2.2 g, 8.9 mmol), sodium methanesulfinate (85%) (1.6 g, 13.3 mmol), CuI (0.2 g, 0.9 mmol), L-proline (0.2 g, 1.8 mmol) and K2CO3 (0.2 g, 1.8 mmol) in DMSO (20 ml) were heated under microwave radiation at 140° C. for 3 h in nitrogen-flushed vials. Water and EtOAc were added. The water layer was extracted with EtOAc (3×100 ml) and the combined organic phases were washed with LiCl (5%), HCl (1 N) and brine. The resulting solution was dried (Na2SO4) and evaporated to dryness. The residue was purified by flash column chromatography (isooctane/EtOAc) to give the title compound (1.7 g). MS m/z (rel. intensity, 70 eV) 244 (M+, bp), 213 (39), 165 (26), 134 (22), 79 (23).

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US08524766B2
출처 데이터셋	uspto-grants-2013_09
ORD ID	ord-4c5db21f63e6492c829c6c16c4269287
출처 메모	uspto-grants-2013_09