Benzyl Bromide → HCID 18970180, compound

HRID 399105Notes

Reaction equation

HRID 399105 reaction equation
[H-].[Na+].[OH:3][CH:4]1[CH2:8][CH2:7][C:6]([C:14]([O:16][CH2:17][CH3:18])=[O:15])([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5]1.[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C>[CH2:19]([O:3][CH:4]1[CH2:8][CH2:7][C:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:5]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 18970186Diethyl 3-hydroxycyclopentane-1,1-dicarboxylate

Product 1

HCID 18970180HCID 18970180, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

Sodium hydride (60% oil dispersion, 2.1 g, 53 mmol) was added in portions to a solution of diethyl 3-hydroxycyclopentane-1,1-dicarboxylate 27 (11 g, 48 mmol), benzyl bromide (9.7 g, 53 mol), and n-tetrabutylammonium iodide (100 mg) in dry DMF (50 mL) at 25° C. (Step 25). The mixture was stirred for 1 hr at 65° C., poured onto ice and then extracted with ether (2×50 mL). The combined either extract was washed with water (3×50 mL) and driedover MgSO4. Chromatography on silica gel (10:90 ethyl acetate/hexane, Rf=0.38) afforded 11.6 g (75%) of the benzyl ether 28; 1H NMR (CDCl3) δ1.3 (t, J=7.2 Hz, 6H, CH3), 1.7-2.7 (m, 6H, CH2), 4.2 (q, J=7.2 Hz, 4H, O=COCH2), 4.1 (m, 1H, O--CH), 4.6 (s, 2H, O--CH2), 7.3 (s, 5H, phenyl).

Workup

  1. additionpoured onto ice
  2. extractionextracted with ether (2×50 mL)
  3. extractionextract
  4. washwas washed with water (3×50 mL)

Sources & evidence

ORD record
ord-83bf0ec410c24e5cb3f614beb0ad8cfe
Source dataset
uspto-grants-1998_10
Patent number
US05817776

Reaction notes

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