Benzyl Bromide → Benzyl 9-(1,3-benzodioxol-5-yl)-8-(benzyloxymethyl)benzo[g][1,3]benzodioxole-7-carboxylate

HRID 2354591Notes

Reaction equation

HRID 2354591 reaction equation
[Na+].[O:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]3[C:12]([CH2:27][OH:28])=[C:13]([C:24]([O-:26])=[O:25])[CH:14]=[C:15]4[C:23]=3[C:19]3[O:20][CH2:21][O:22][C:18]=3[CH:17]=[CH:16]4)=[CH:10][C:5]=2[O:4][CH2:3]1.[CH2:29](Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[OH-].[K+]>O>[CH2:29]([O:25][C:24]([C:13]1[CH:14]=[C:15]2[C:23](=[C:11]([C:9]3[CH:8]=[CH:7][C:6]4[O:2][CH2:3][O:4][C:5]=4[CH:10]=3)[C:12]=1[CH2:27][O:28][CH2:11][C:9]1[CH:10]=[CH:5][CH:6]=[CH:7][CH:8]=1)[C:19]1[O:20][CH2:21][O:22][C:18]=1[CH:17]=[CH:16]2)=[O:26])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 23670370HCID 23670370, compound

Product 1

HCID 5273778Benzyl 9-(1,3-benzodioxol-5-yl)-8-(benzyloxymethyl)benzo[g][1,3]benzodioxole-7-carboxylateYield 102.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 3 (78 mg, 0.2 mmol) and benzyl bromide (0.38 mL, 3.2 mmol), and powdered KOH (168 mg) was heated at 140° C. for 3 h, and then cooled to room temperature. The mixture was diluted with water (100 mL) and extracted with EtOAc (3×100 mL). The extract was washed with water (3×100 mL), dried over MgSO4, and concentrated in vacuo. The residue was purified by column chromatography on silica gel using CH2Cl2 to give 4 (56 mg, 51%) as a colorless liquid. 1H NMR (CDCl3) δ 8.27 (s, 1H, H4), 7.51 (d, 1H, H5, J=8.4 Hz), 7.23-7.44 (m, 10H, 2×OCH2Ph), 7.22 (d, 1H, H6, J=8.4 Hz), 6.82 (d, 1H, H5′, J=7.8 Hz), 6.77 (d, 1H, H2′, J=1.5 Hz), 6.71 (dd, 1H, H6′, J=1.5, 7.8 Hz), 6.05 (AB, 2H, 3′,4′-OCH2O—, Δδ=10.2 Hz, J=1.2 Hz), 5.84 (AB, 2H, 7,8-OCH2O—, Δδ=4.8 Hz, J=1.2 Hz), 5.34 (s, 2H, 3-COOCH2Ph), 4.67 (s, 2H, 2-CH2OCH2Ph), 4.32 (s, 2H, 2-CH2OBn); MS (EI) m/z 546 [M]+.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with EtOAc (3×100 mL)
  3. washThe extract was washed with water (3×100 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-84f645ee35d04575bb27580ef361b897
Source dataset
uspto-grants-2010_07
Patent number
US07754718B2

Reaction notes

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