Benzyl Bromide → 1-[3-(Benzyloxy)-2-[(benzyloxy)methyl]-2-(4-bromobenzyl)propyl]-4-(diethoxymethyl)benzene

HRID 566509Notes

Reaction equation

[Br:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][C:7]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([CH:19]([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22])=[CH:15][CH:14]=2)([CH2:10][OH:11])[CH2:8][OH:9])=[CH:4][CH:3]=1.[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[H-].[Na+]>CN(C=O)C>[CH2:28]([O:9][CH2:8][C:7]([CH2:10][O:11][CH2:6][C:5]1[CH:26]=[CH:27][CH:2]=[CH:3][CH:4]=1)([CH2:6][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:27][CH:26]=1)[CH2:12][C:13]1[CH:14]=[CH:15][C:16]([CH:19]([O:20][CH2:21][CH3:22])[O:23][CH2:24][CH3:25])=[CH:17][CH:18]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 2-(4-Bromobenzyl)-2-[4-(diethoxymethyl)benzyl]-1,3-propanediol(3 g, crude), benzyl bromide (3 mL), and NaH (1.2 g, 60% in mineral oil) in 30 mL of DMF was stirred for 14 h at 70° C. The mixture was then quenched with 5 mL of MeOH followed by 50 mL of saturated NH4Cl and extracted with 200 mL of 2:1 hexane/EtOAc. The extract was dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography eluted with 15:1 hexane EtOAc containing 1% of Et3N to give 2.5 g of the title compound as an oil.

Workup

customThe mixture was then quenched with 5 mL of MeOH
extractionextracted with 200 mL of 2:1 hexane/EtOAc
dry with materialThe extract was dried over Na2SO4
concentrationconcentrated
customThe residue was purified by silica gel chromatography
washeluted with 15:1 hexane EtOAc containing 1% of Et3N

Sources & evidence

ORD record: ord-1ee26cce31874b15b18e200ab3ca88e7
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06174874B1

Reaction notes

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