Benzyl Chloride → HCID 57572477, compound

HRID 1038287Notes

Reaction equation

[OH:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]([C:11]([OH:13])=[O:12])=[CH:4][C:3]=1[C:14]([OH:16])=[O:15].[CH2:17](Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:17]([O:9][C:8]([C:7]1[CH:6]=[C:5]([C:11]([O:13][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:12])[CH:4]=[C:3]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[C:2]=1[O:1][CH2:14][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=1)=[O:10])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 75 °C

Procedure

Compound 13 (22.6 g, 0.1 mol), benzyl chloride (57 g, 0.46 mol) and anhydrous potassium carbonate (120 g, 0.87 mol) were mixed in dry DMF (500 mL). The mixture was heated at 75° C. while stirring under nitrogen overnight. TLC confirmed that the reaction was complete. The reaction mixture was cooled, filtered, and the filtrate was evaporated to remove the volatiles. The residue was dissolved in 1 L of recycling [?] methylene chloride and a silica gel plug was used to remove some impurities with low Rf. The fully benzyl-protected product was obtained as a thick, yellow oil after removing the solvent: raw yield 53 g (90%).

Workup

temperatureThe reaction mixture was cooled
filtrationfiltered
customthe filtrate was evaporated
customto remove the volatiles
dissolutionThe residue was dissolved in 1 L
customto remove some impurities with low Rf
customwas obtained as a thick, yellow oil
customafter removing the solvent

Sources & evidence

ORD record: ord-51a40e008c1745f58a07f42d6a361044
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08551453B2

Reaction notes

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