Benzyl Bromide → HCID 23256317, compound

HRID 363503Notes

Reaction equation

HRID 363503 reaction equation
[CH:1]([C@@:3]1([CH2:9][OH:10])[O:7][C:6](=[O:8])[CH2:5][CH2:4]1)=[CH2:2].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CN(C=O)C.[Ag-]=O>[CH2:11]([O:10][CH2:9][C:3]1([CH:1]=[CH2:2])[O:7][C:6](=[O:8])[CH2:5][CH2:4]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 7498Benzyl BromideHCID 10534761HCID 10534761, compound

Product 1

HCID 23256317HCID 23256317, compoundYield 80.1%

Reagents, catalysts & solvents 2

HCID 178418778HCID 178418778, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 2.13 (0.140 g, 1.0 mmol) in DMF (5 mL) was stirred with silver(I) oxide (0.232 g, 1.0 mmol) and benzyl bromide (0.3 mL, 2.5 mmol) for 5 days at room temperature. The reaction mixture was filtered, diluted with water, and extracted thrice with EtOAc. The organic layer was washed with water, dried (Na2SO4), and concentrated. The residue was purified by flash column chromatography over silica gel with hexanes:EtOAc (2:1) as eluant to give the intermediate 5-[(benzyloxy)methyl]-5-vinyl-tetrahydro-2-furanone (0.186 g, 80%) as an oil; [α]22D -29.68° (c 3.08, CHCl3); IR (neat) 1772 (C=O) and 1653 cm-1 (C=C); 1H NMR (CDCl3) δ 2.05 (m, 1 H, H-4a), 2.35-2.74 (m, 3 H, H-4b, H-3), 3.55 (AB q, J=10.4 Hz, 2 H, CH2OH), 4.60 (AB q, J=12.0 Hz, 2 H, CH2OCH2Ph), 5.22 (dd, J=10.9, 0.5 Hz, 1 H, CH=CHH), 5.37 (dd, J=17.3, 0.6 Hz, 1 H, CH=CHH), 5.88 (dd, J=17.3, 10.9 Hz, 1 H, CH=CH2); 13C NMR (CDCl3) δ 28.88, 29.37, 73.66, 74.50, 86.81, 115.73, 127.58, 127.80, 128.46, 136.72, 137.65, 176.82. Anal. Calcd for C14H16O3 : C, 72.39; H, 6.94. Found: C, 72.62; H, 6.92.

Workup

  1. filtrationThe reaction mixture was filtered
  2. additiondiluted with water
  3. extractionextracted thrice with EtOAc
  4. washThe organic layer was washed with water
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography over silica gel with hexanes:EtOAc (2:1) as eluant

Sources & evidence

ORD record
ord-03ae91bcb54b4ca990146202842e0cf6
Source dataset
uspto-grants-1999_02
Patent number
US05874464

Reaction notes

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