Sodium t-butoxide → HCID 66974911, compound

HRID 1022530Notes

Reaction equation

HRID 1022530 reaction equation
[CH2:1]([N:8]([CH2:13][CH:14]([CH2:25][O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[CH:15]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=1)[OH:16])[C:9](=[O:12])[CH2:10]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[Na+]>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH:14]([CH2:25][O:26][Si:27]([C:30]([CH3:32])([CH3:33])[CH3:31])([CH3:29])[CH3:28])[CH:15]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=2)[O:16][CH2:10][C:9]1=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 23676156Sodium t-butoxideHCID 66975664HCID 66975664, compound

Product 1

HCID 66974911HCID 66974911, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-benzyl-N-[(2RS,3RS)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-3-(3,4-dichlorophenyl)-3-hydroxypropyl]-2-chloroacetamide (2.72 g) in THF (100 ml) was added sodium tert-butoxide (621 mg) under ice-cooling, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with ethyl acetate. The diluted solution was washed with distilled water and brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give the title compound (2.51 g).

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthe residue was diluted with ethyl acetate
  4. washThe diluted solution was washed with distilled water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b4de623858474c1bb57d5ec95fba86a2
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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