tert-Butyldimethylsilyl chloride → HCID 59596567, compound

HRID 2264956Notes

Reaction equation

HRID 2264956 reaction equation
[C:1]([Si:5]([CH3:8])([CH3:7])Cl)([CH3:4])([CH3:3])[CH3:2].Cl.[O:10]1[CH2:14][CH:13]([OH:15])[CH2:12][NH:11]1>CN(C=O)C>[C:1]([Si:5]([CH3:8])([CH3:7])[O:15][CH:13]1[CH2:14][O:10][NH:11][CH2:12]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 129324731,2-Oxazolidin-4-ol--hydrogen chloride (1/1)

Product 1

HCID 59596567HCID 59596567, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-Butyl-dimethyl-chlorosilane (0.5 g, 3.21 mmol) was added to a stirred solution of isoxazolidin-4-ol hydrochloride (0.40 g, 3.18 mmol) in DMF (3 mL). The mixture was left to stir at ambient temperature for 2.5 hours before the solvent was evaporated and the resultant residue partitioned between ethyl acetate (50 mL) and water (20 mL). The organic phase was separated and washed with water (3×20 mL) then brine (20 mL), dried (MgSO4), filtered and evaporated to provide the desired product as a colourless oil (0.62 g, 96%). 1H NMR (CDCl3, 400 MHz) 5.52 (s, 1H), 4.60-4.65 (m, 1H), 3.45-3.62 (m, 1H), 3.80-4.05 (m, 1H), 2.80-3.05 (m, 2H), 0.80 (s, 9H), 0.08 (s, 6H).

Workup

  1. waitThe mixture was left
  2. customwas evaporated
  3. customthe resultant residue partitioned between ethyl acetate (50 mL) and water (20 mL)
  4. customThe organic phase was separated
  5. washwashed with water (3×20 mL)
  6. dry with materialbrine (20 mL), dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-ce8cdc3eb69547c19aff799da755fb5f
Source dataset
uspto-grants-2010_12
Patent number
US07855216B2

Reaction notes

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