Water → HCID 58492433, compound

HRID 2047971Notes

Reaction equation

HRID 2047971 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][O:9]2)=[CH:4][C:3]=1[C:12](=[O:14])[CH3:13].[H-].[Na+].I[CH2:18][CH2:19][CH3:20].O>CN(C=O)C>[CH2:18]([O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][O:9]2)=[CH:4][C:3]=1[C:12](=[O:14])[CH3:13])[CH2:19][CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 537585521-(3,4-Dihydro-7-hydroxy-2H-1-benzopyran-6-yl)ethanone

Product 1

HCID 58492433HCID 58492433, compoundYield 114.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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).

Workup

  1. stirringstirred at room temperature for 3 hours
  2. extractionfollowed by extraction
  3. concentrationThe thus-obtained organic layer was concentrated to dryness under reduced pressure
  4. customthe residue was then purified
  5. concentrationThe purified product was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-6f66553cb8004f97a8f26b8593eaaf21
Source dataset
uspto-grants-2013_11
Patent number
US08592593B2

Reaction notes

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