Water → 4-Allyloxy-2-ethoxy-1,3-benzodioxolane

HRID 218264Notes

Reaction equation

HRID 218264 reaction equation
[CH2:1]([O:3][CH:4]1[O:8][C:7]2[CH:9]=[CH:10][CH:11]=[C:12]([OH:13])[C:6]=2[O:5]1)[CH3:2].[H-].[Na+].[CH2:16](Br)[CH:17]=[CH2:18].O>CN(C=O)C>[CH2:18]([O:13][C:12]1[C:6]2[O:5][CH:4]([O:3][CH2:1][CH3:2])[O:8][C:7]=2[CH:9]=[CH:10][CH:11]=1)[CH:17]=[CH2:16]

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 134470632-Ethoxy-benzo[1,3]dioxol-4-ol

Product 1

HCID 699337744-Allyloxy-2-ethoxy-1,3-benzodioxolane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 37 (4.0 g, 22.0 mmol) in DMF (7 mL) was added dropwise over 5 min to a suspension of sodium hydride (1.32 g, 33.0 mmol 60% dispersion in oil) in DMF (15 mL) at 0° C. The reaction mixture was stirred at this temperature for 15 min, then allyl bromide (2.93 g, 2.09 mL, 24.2 mmol) was added and the reaction mixture was allowed to warm to rt over 16 h. The reaction mixture was then cooled to 0° C., water was added dropwise, then the reaction mixture was extracted with t-BuOMe (3×). The organic phase was washed successively with water and brine, dried (Na2SO4) and evaporated to dryness to give 4.8 g of crude product. Purification by column chromatography (SiO2 2:98 EtOAc:cyclohexane) gave 38 compound (3.3 g, 68%):

Workup

  1. temperatureThe reaction mixture was then cooled to 0° C.
  2. extractionthe reaction mixture was extracted with t-BuOMe (3×)
  3. washThe organic phase was washed successively with water and brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated to dryness
  6. customto give 4.8 g of crude product
  7. customPurification by column chromatography (SiO2 2:98 EtOAc:cyclohexane)

Sources & evidence

ORD record
ord-2a25e37172664dd499c230b08964c9af
Source dataset
uspto-grants-2012_06
Patent number
US08198302B2

Reaction notes

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