4-Methylmorpholine → 1-(t-Butyldimethylsilyloxy)-2-(p-nitrophenoxycarbonyloxy)ethane

HRID 1737104Notes

Reaction equation

HRID 1737104 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:7]([O:8][C:9](Cl)=[O:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Si:14]([O:21][CH2:22][CH2:23][OH:24])([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15].CN1CCOCC1>C(Cl)Cl>[Si:14]([O:21][CH2:22][CH2:23][O:24][C:9]([O:8][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:13][CH:12]=1)=[O:10])([C:17]([CH3:19])([CH3:20])[CH3:18])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 821294-Nitrophenyl chloroformateHCID 111376652-(tert-Butyl(dimethyl)silyl)oxyethanol

Product 1

HCID 189396641-(t-Butyldimethylsilyloxy)-2-(p-nitrophenoxycarbonyloxy)ethane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A 604 mg (3.00 mmol) sample of p-nitrophenoxycarbonylchloride in 3 mL of methylene chloride was added to a solution of 0.528 g (3.00 mmol) of 2-(t-butyldimethylsilyloxy)ethanol and 0.330 mL of 4-methylmorpholine in 2 mL of methylene chloride cooled in an ice bath. The solution was stirred for 2 hours. The mixture was diluted with methylene chloride, which was washed with water, dried and concentrated. The crude product was chromatographed on silica gel, eluting with 10% ethyl acetate in hexane. The solvent was removed and the product dried to afford 0.453 g of the title compound, which was taken directly to the next step.

Workup

  1. temperaturecooled in an ice bath
  2. washwas washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe crude product was chromatographed on silica gel
  6. washeluting with 10% ethyl acetate in hexane
  7. customThe solvent was removed
  8. customthe product dried

Sources & evidence

ORD record
ord-9a1d85646ba44350b35534f69f87d771
Source dataset
uspto-grants-1996_07
Patent number
US05541334

Reaction notes

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