ChemicalBook CAS DataBase List 5-ACETYL-2,3-DIHYDROBENZO(B)FURAN

5-ACETYL-2,3-DIHYDROBENZO(B)FURAN synthesis

7synthesis methods

Product Name:5-ACETYL-2,3-DIHYDROBENZO(B)FURAN
CAS Number:90843-31-5
Molecular formula:C10H10O2
Molecular Weight:162.19

1191-99-7
329 suppliers
$10.00/10g

75-36-5 Synthesis

75-36-5
579 suppliers
$17.92/100G

90843-31-5
150 suppliers
$52.29/0.5g

Yield: 93%

Reaction Conditions:

tin(IV) chloride in (2S)-N-methyl-1-phenylpropan-2-amine hydrate;dichloromethane

Steps:

162.A 5-Acetyl-2,3-dihydrobenzofuran
EXAMPLE 162A 5-Acetyl-2,3-dihydrobenzofuran To a 0° C. solution of acetyl chloride (1.64 mL, 23.0 mmol, 1.3 equivalents) in methylene chloride (30 mL) was added stannic chloride (2.49 mL, 21.3 mmol, 1.2 equivalents), maintaining the temperature below 5° C. The solution was stirred 15 minutes at 0° C., and then a solution of 2,3-dihydrofuran (2.00 mL, 17.7 mmol) in methylene chloride (5 mL) was added dropwise while maintaining the temperature below 8° C. The dark red solution was stirred 1 hour at 2° C. and then poured into 50 mL of ice water. The reaction was stirred an additional 30 minutes, and the layers were separated. The organic layer was washed with water and aqueous sodium bicarbonate, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on 150 9 silica gel, eluding with 18% ethyl acetate in hexanes. The solvents were removed under reduced pressure to yield the title compound (2.68 g, 93%) as a yellow solid.

References:

Abbott Laboratories US6162927, 2000, A

496-16-2 Synthesis