Benzyl Bromide → HCID 18970178, compound

HRID 2393939Notes

Reaction equation

HRID 2393939 reaction equation
[H-].[Na+].[OH:3][CH2:4][CH:5]1[CH2:8][C:7]([C:13]([O:15][CH3:16])=[O:14])([C:9]([O:11][CH3:12])=[O:10])[CH2:6]1.[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C>[CH2:17]([O:3][CH2:4][CH:5]1[CH2:6][C:7]([C:9]([O:11][CH3:12])=[O:10])([C:13]([O:15][CH3:16])=[O:14])[CH2:8]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 18977619HCID 18977619, compound

Product 1

HCID 18970178HCID 18970178, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

Sodium hydride (60% oil dispersion, 2.1 g, 53 mmol) is added in portions to a solution of dimethyl 3-(hydroxymethyl)cyclobutane-1,1-dicarboxylate (51), benzyl bromide, and n-tetrabutylammonium iodide in dry DMF at 25° C. (Step 47). The mixture is stirred for 1 hr at 65° C., poured onto ice and then extracted with ether (2×50 mL). The combined ether extract is washed with water (3×50 mL) and dried over MgSO4. Chromatography on silica gel.

Workup

  1. additionpoured onto ice
  2. extractionextracted with ether (2×50 mL)
  3. extractionThe combined ether extract
  4. washis washed with water (3×50 mL)
  5. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-544a2c4bdc8d4ec8a6a5686ac499343c
Source dataset
uspto-grants-1998_09
Patent number
US05808146

Reaction notes

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