Allyl bromide → 5-[(Prop-2-en-1-yl)oxy]-2,3-dihydro-1H-inden-1-one

HRID 2252228Notes

Reaction equation

HRID 2252228 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.[H-].[Na+].[CH2:14](Br)[CH:15]=[CH2:16]>C1COCC1.CN(C=O)C>[CH2:16]([O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2)[CH:15]=[CH2:14]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 2331475-Hydroxy-1-indanone

Product 1

HCID 223249215-[(Prop-2-en-1-yl)oxy]-2,3-dihydro-1H-inden-1-oneYield 79.1%

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

To a solution of 5-hydroxy-1-indanone (4.27 g, 0.0288 mol) in THF/DMF (5 mL/10 mL) at 0° C. was added NaH (60%, 1.21 g, 0.0303 mol) followed by allyl bromide (2.7 mL, 0.0317 mol). The reaction was warmed to room temperature and stirred overnight The reaction mixture was quenched with water and extracted with EtOAc, washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by flash chromatography eluted with EtOAc/hexane (1:1) to give 4.29 g (79%) of the desired product as brown oil. MS (DCI/NH3) m/z: 189.1 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 2.53-2.64 (m, 2H), 2.96-3.11 (m, 2H), 4.64-4.72 (m, 2H), 5.29 (dd, J=10.51, 1.36 Hz, 1H), 5.42 (dd, J=17.29, 1.70 Hz, 1H), 6.06 (m, 1H), 6.98 (dd, J=8.48, 2.37 Hz, 1H), 7.10 (d, J=2.03 Hz, 1H) 7.56 (d, J=8.48 Hz, 1H).

Workup

  1. customwas quenched with water
  2. extractionextracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography
  8. washeluted with EtOAc/hexane (1:1)

Sources & evidence

ORD record
ord-9bb2ab864282400e8aabf2d3c10c6955
Source dataset
uspto-grants-2008_01
Patent number
US07320986B2

Reaction notes

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