Triethylamine → O-(tert-Butyldiphenylsilyl)hydroxylamine

HRID 1788677Notes

Reaction equation

HRID 1788677 reaction equation
Cl.[NH2:2][OH:3].C(N(CC)CC)C.[Si:11](Cl)([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CN(C=O)C>[Si:11]([O:3][NH2:2])([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94078tert-ButyldiphenylchlorosilaneHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 11737343O-(tert-Butyldiphenylsilyl)hydroxylamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Hydroxylamine hydrochloride (3.48 g) and triethylamine (7 ml) were stirred for 0.25 hours in DMF (50 ml) at 0° C. tert-Butyldiphenylsilyl chloride (13 ml) was added and the mixture was stirred for 1 hour. The mixture was partitioned between pentane (500 ml) and water (100 ml), the layers separated and the aqueous phase extracted with ethyl acetate (2×100 ml). The organic layers were combined, washed with brine (50 ml), dried over magnesium sulphate and the solvent was removed in vacuo. The crude product was triturated with pentane (20 ml) yielding the pure title compound as white solid (4.04 g), m.p.t. 85°-87° C.

Workup

  1. additionwas added
  2. customThe mixture was partitioned between pentane (500 ml) and water (100 ml)
  3. customthe layers separated
  4. extractionthe aqueous phase extracted with ethyl acetate (2×100 ml)
  5. washwashed with brine (50 ml)
  6. dry with materialdried over magnesium sulphate
  7. customthe solvent was removed in vacuo
  8. customThe crude product was triturated with pentane (20 ml)

Sources & evidence

ORD record
ord-87387689be1e4fb4aa903dde6aeb2236
Source dataset
uspto-grants-1987_08
Patent number
US04684641

Reaction notes

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