Sulfuric Acid → HCID 22161962、化合物

To a solution of 5-hydroxy-2,3-dihydrobenzothiophene (500 mg, 3.28 mmoles) in 20 mL benzene in a sealable tube was added t-butanol (729 mg, 9.84 mmoles, 3.0 eq) and 0.4 mL concentrated H2SO4. The tube was sealed and the reaction mixture heated at 60° C. for 24 hours. The reaction mixture was cooled, diluted with water (50 mL) and extracted 2×25 mL ether. The combined extracts were washed with sodium bicarbonate (1×25 mL), H2O (1×25 mL) and brine (1×25 mL). The organic layer was then dried over Na2SO4, filtered and concentrated to give 220 mg crude product. Purification by flash chromatography (90/10, hexane/EtOAc) afforded 125 mg pure product (18%) mp 90°-93° C.

1. customThe tube was sealed
2. temperatureThe reaction mixture was cooled
3. extractionextracted 2×25 mL ether
4. washThe combined extracts were washed with sodium bicarbonate (1×25 mL), H2O (1×25 mL) and brine (1×25 mL)
5. dry with materialThe organic layer was then dried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated
8. customto give 220 mg crude product
9. customPurification by flash chromatography (90/10, hexane/EtOAc)

ORDレコード

ord-951cb797abb449dcaf093ef3d2ec5d6f

出典データセット

uspto-grants-1990_10

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US04963580