Hydrochloric Acid → HCID 53256645, compound

HRID 1959961Notes

Reaction equation

HRID 1959961 reaction equation
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[O:3]1.Br[CH2:18][CH2:19][O:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][O:22]1.[H-].[Na+].Cl>O.C(OCC)(=O)C.CN(C)C=O>[CH3:8][C:6]1([CH3:7])[C:2]([CH3:16])([CH3:1])[O:3][B:4]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:18][CH2:19][O:20][CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][O:22]3)=[CH:11][CH:10]=2)[O:5]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 27346244-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Product 1

HCID 53256645HCID 53256645, compoundYield 84%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Into dimethylformamide (250 mL), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (10.0 g, 45.5 mmol) and 2-(2-bromoethoxy)tetrahydro-2H-pyran (10.0 g, 45.5 mmol) were dissolved, to which 60% sodium hydride in oil (2.98 g, 68.3 mmol) was added while cooling with ice, followed by stirring for three hours while cooling with ice, and further for 17 hours at room temperature. Ethyl acetate was then added, and excess hydrated sodium was neutralized with 1M hydrochloric acid. Further, water was added and the resulting solution was separated. The resulting organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (hexane:ethyl acetate, 100:0-70:30, V/V) to give the desired title compound (13.3 g, yield 84%).

Workup

  1. additionwas added
  2. temperaturewhile cooling with ice
  3. temperaturewhile cooling with ice
  4. waitfurther for 17 hours at room temperature
  5. customthe resulting solution was separated
  6. washThe resulting organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customThe residue thus obtained
  10. customwas purified by silica gel column chromatography (hexane:ethyl acetate, 100:0-70:30, V/V)

Sources & evidence

ORD record
ord-24afb0330d2144c3b37bc428cc11b6ec
Source dataset
uspto-grants-2013_04
Patent number
US08410273B2

Reaction notes

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