Sodium hydride → HCID 57558159, compound

HRID 1162955Notes

Reaction equation

HRID 1162955 reaction equation
[H-].[Na+].[CH2:3]1[O:8][CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:6][CH2:5][CH:4]1[OH:15].Br[CH2:17][CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21].[Cl-].[NH4+]>CN(C=O)C>[C:23]([Si:20]([CH3:22])([CH3:21])[O:19][CH2:18][CH2:17][O:15][CH:4]1[CH2:3][O:8][CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:6][CH2:5]1)([CH3:26])([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 743621,3-Dioxan-5-ol, 2-phenyl-HCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilane

Product 1

HCID 57558159HCID 57558159, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (133 mg, 3.32 mmol) was added to 5 mL of a solution of cis-1,3-O-benzylideneglycerol (300 mg, 1.66 mmol) in DMF, and the mixture was stirred at room temperature for two hours. (2-bromoethoxy)-tert-butyldimethylsilane (534 μl, 3.32 mmol) was added to the mixture which was then stirred at room temperature for two hours. Aqueous saturated ammonium chloride was added to the mixture, followed by extraction with ethyl acetate. The extract was washed with saturated saline and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain a crude product, tert-butyldimethyl-[2-(2-phenyl-[1,3]dioxan-5-yloxy)ethoxy]silane (343 mg) as a colorless oil.

Workup

  1. stirringwas then stirred at room temperature for two hours
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe extract was washed with saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6f8e057bb5d3400f99a5216b22f6d7c3
Source dataset
uspto-grants-2010_10
Patent number
US07820693B2

Reaction notes

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