Allyl bromide → 4-(Allyloxy)-2,3-dihydro-1H-indene

HRID 13911Notes

Reaction equation

HRID 13911 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]1[C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([OH:16])[C:10]=2[CH2:9][CH2:8]1.[CH2:17](Br)[CH:18]=[CH2:19]>CN(C)C=O.O>[CH2:19]([O:16][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:10]=1[CH2:9][CH2:8][CH2:7]2)[CH:18]=[CH2:17]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 742334-Hydroxyindan

Product 1

HCID 685848044-(Allyloxy)-2,3-dihydro-1H-indene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of potassium carbonate (23.49 g, 0.170 mol) in N,N-dimethylformamide (350 mL) was added indan-4-ol (7.60 g, 0.057 mol) followed by allyl bromide (8.22 g, 0.068 mol) and the reaction mixture was allowed to stir at room temperature for 12 h. The reaction mixture was diluted with water (1000 mL) to dissolve any solids and extracted with diethyl ether (3×250 mL). The combined organic layers were washed with water (4×500 mL), aqueous sodium chloride (400 mL), dried (magnesium sulfate) and the solvent was removed in vacuo to give 4-(allyloxy)indane. The allyl ether was dissolved in mesitylene (40 mL) and heated at reflux for 8 h. Removal of the solvent in vacuo provided 5-allylindan-4-ol, which was re-dissolved in N,N-dimethylformamide (250 mL). Potassium carbonate (14.28 g, 0.103 mol), benzyl bromide (6.48 g, 0.038 mol), and tetrabutylammonium iodide (2.54 g, 0.007 mol) were added to the reaction mixture. The reaction mixture was allowed to stir at room temperature for 12 h. The reaction mixture was diluted with water (1000 mL) to dissolve any solids and extracted with diethyl ether (3×250 mL). The combined organic layers were washed with water (4×500 mL), aqueous sodium chloride (400 mL), dried (magnesium sulfate) and the solvent was removed in vacuo to give a crude oil. Purification by flash column chromatography (silica, ethyl acetate:hexanes 1:9) provided 10.22 g (68%) of 5-allyl-2,3-dihydro-1H-inden-4-yl benzyl ether as a pale yellow oil. Rf=0.45 (silica, ethyl acetate:hexanes 1:19); Anal. calcd. for C19H20O: C, 86.32; H, 7.63. Found: C, 85.90; H, 7.49.

Workup

  1. dissolutionto dissolve any solids
  2. extractionextracted with diethyl ether (3×250 mL)
  3. washThe combined organic layers were washed with water (4×500 mL), aqueous sodium chloride (400 mL)
  4. dry with materialdried (magnesium sulfate)
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-0073296be60345cca74feff931ba75ef
Source dataset
uspto-grants-2010_06
Patent number
US07728155B2

Reaction notes

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