Reaction #155316

Reaction equation

Water

Sodium hydride

1-(7-Hydroxychroman-6-yl)ethanone

1-Iodopropane

→

1-(7-propoxychroman-6-yl)ethanone

Yield 114.9%

Solvents

DMF

Conditions

Workup

1. 1
   workup.STIRRINGstirred at room temperature for 3 hours
2. 2
   Extractionfollowed by extraction
3. 3
   ConcentrationThe thus-obtained organic layer was concentrated to dryness under reduced pressure
4. 4
   Otherthe residue was then purified
5. 5
   ConcentrationThe purified product was concentrated to dryness under reduced pressure

Procedure

1-(7-Hydroxychroman-6-yl)ethanone (3.0 g, 15.6 mmol) was dissolved in DMF (20 ml). Sodium hydride (60% oil base, 686 mg, 1.1 equivalent weight) was added thereto while ice cooling, and then stirred for 10 minutes. 1-Iodopropane (2.92 g, 1.1 equivalent weight) was added to the mixture and then stirred at room temperature for 3 hours. Water was added to the reaction mixture, followed by extraction using ethyl acetate. The thus-obtained organic layer was concentrated to dryness under reduced pressure, and the residue was then purified using silica gel column chromatography (n-hexane:ethyl acetate=1:0→0:1). The purified product was concentrated to dryness under reduced pressure, giving a white powder of 1-(7-propoxychroman-6-yl)ethanone (4.2 g, yield: quantitative).

Source