Benzyl Bromide → HCID 11683652, compound

HRID 1422552Notes

Reaction equation

HRID 1422552 reaction equation
[Si:1]([O:8][CH2:9][C@H:10]1[O:15][CH:14]=[CH:13][C@@H:12]([OH:16])[C@@H:11]1[OH:17])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH-].[Na+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>ClCCl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:20]([O:16][C@H:12]1[C@H:11]([O:17][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C@@H:10]([CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[O:15][CH:14]=[CH:13]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 110216286-O-(tert-Butyldimethylsilyl)-D-glucal

Product 1

HCID 11683652HCID 11683652, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

6-O-tert-butyldimethylsilyl-D-glucal (11.5 mmol) was dissolved in dichloromethane (30 mL). Sodium hydroxide (23 mmol) followed by tetrabutylammonium bromide (5 mg) and benzyl bromide (27 mmol) were added and the reaction mixture was stirred at 40° C. After reaction was completed the reaction mixture was cooled down, solids were filtered off, filtrate was diluted with dichloromethane (100 mL), washed with water until neutral and dried over anhydrous sodium sulfate. Drying agent and solvents were removed and product was separated using column chromatography (SilicaGel 60) and hexanes:ethyl acetate as eluents. 3,4-di-O-benzyl-6-O-tert-butyldimethylsilyl-D-glucal (6.9 mmol, yield 60%) was obtained. [α]D−6.6 (c=1, chloroform).

Workup

  1. additionwere added
  2. customAfter reaction
  3. temperaturewas cooled down
  4. filtrationsolids were filtered off
  5. additionfiltrate was diluted with dichloromethane (100 mL)
  6. washwashed with water until neutral and
  7. dry with materialdried over anhydrous sodium sulfate
  8. customDrying agent and solvents
  9. customwere removed
  10. customproduct was separated

Sources & evidence

ORD record
ord-e6e13282edb748bcaa328de10cbf7069
Source dataset
uspto-grants-2015_01
Patent number
US08927506B2

Reaction notes

Loading…