Benzyl Bromide → HCID 11048568, compound

HRID 380249Notes

Reaction equation

HRID 380249 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][O:8][C@H:9]2[C@@H:14]([OH:15])[C@@H:13]([CH2:16][OH:17])[O:12][CH:11]=[CH:10]2)=[CH:5][CH:4]=1.[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[H-].[Na+]>CN(C=O)C.O>[CH2:20]([O:15][C@H:14]1[C@@H:13]([CH2:16][O:17][CH2:7][C:6]2[CH:18]=[CH:19][CH:3]=[CH:4][CH:5]=2)[O:12][CH:11]=[CH:10][C@H:9]1[O:8][CH2:7][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:19][CH:18]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 12047169HCID 12047169, compound

Product 1

HCID 11048568HCID 11048568, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 3-O-(4-methoxybenzyl)-D-galactal (2.28 g, 8.56 mmol) and benzyl bromide (3.75 mL, 3.68 mol equiv; freshly passed through basic alumina) in DMF (30 mL) under N2 at 0° C. was treated with NaH (1.37 g, 4.0 mol equiv) in two portions. The reaction was stirred 0.5 h at 0° C. and 1 h at rt. The reaction was carefully poured into 50 g of crushed ice, diluted to 100 mL with water, then extracted with EtOAc-hexanes (1:1, 100 mL×3). Organic extracts were washed with water (100 mL×2), dried (Na2SO4) and concentrated. Flash chromatography with 15% EtOAc-hexanes gave 3.58 g (94%) of the title compound as a clear liquid.

Workup

  1. customat 0° C.
  2. extractionextracted with EtOAc-hexanes (1:1, 100 mL×3)
  3. washOrganic extracts were washed with water (100 mL×2)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ffd8774747fa44e690aa34ef38182963
Source dataset
uspto-grants-2001_10
Patent number
US06303120B1

Reaction notes

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