tert-Butyldimethylsilyl chloride → 1-(t-Butyldimethylsilyloxy)-3-dimethylamino-2-propanol

HRID 638767Notes

Reaction equation

HRID 638767 reaction equation
COC1C=CC(C([O:22][CH2:23][CH:24]([OH:29])[CH2:25][N:26]([CH3:28])[CH3:27])(C2C=CC=CC=2)C2C=CC(OC)=CC=2)=CC=1.C(N(CC)C(C)C)(C)C.[C:41]([Si:45]([CH3:48])([CH3:47])Cl)([CH3:44])([CH3:43])[CH3:42]>CN(C)C=O>[Si:45]([O:22][CH2:23][CH:24]([OH:29])[CH2:25][N:26]([CH3:27])[CH3:28])([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:48])[CH3:47]

Participants

5

Reactant 3

HCID 28928tert-Butyldimethylsilyl chloride2×HCID 81531DiisopropylethylamineHCID 597532281-(4,4'-Dimethoxytrityloxy)-3-dimethylamino-2-propanol

Product 1

HCID 866179491-(t-Butyldimethylsilyloxy)-3-dimethylamino-2-propanol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

3-Dimethylamino-1,2-propanediol (5), (50.1 g, 420.4 mmol) was weighed into a 2 L round bottomed flask with a stir bar. The flask was sealed, flushed with argon, charged with N,N-dimethylformamide (750 mL) and N,N-diisopropylethylamine (111 mL, 630.7 mmol) and cooled to 0° C. t-Butyldimethylchlorosilane (67.0 g, 1.05 equiv.) was weighed into a 500 mL round bottomed flask, sealed and then dissolved in N,N-dimethylformamide (250 mL). The t-butyldimethylchlorosilane solution was transferred to a pressure equalizing dropping funnel and added to the stirring reaction mixture slowly over 20 minutes. The reaction was allowed to come to room temperature while stirring over 3 hours. The reaction was concentrated in vacuo. Saturated bicarbonate (1500 mL) was added to the residue and the mixture transferred to a 4 L separatory funnel. The aqueous phase was extracted with ethyl acetate (3×500 mL). The organic phases were combined, dried over MgSO4, filtered, concentrated and dried under high vacuum to afford 97.81 g (99.7%) of clear, colorless oil that was used without further purification.

Workup

  1. customThe flask was sealed
  2. customflushed with argon
  3. customwas weighed into a 500 mL round bottomed flask
  4. customsealed
  5. additionadded to the stirring reaction mixture slowly over 20 minutes
  6. customto come to room temperature
  7. concentrationThe reaction was concentrated in vacuo
  8. additionSaturated bicarbonate (1500 mL) was added to the residue
  9. customthe mixture transferred to a 4 L separatory funnel
  10. extractionThe aqueous phase was extracted with ethyl acetate (3×500 mL)
  11. dry with materialdried over MgSO4
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customdried under high vacuum
  15. customto afford 97.81 g (99.7%) of clear, colorless oil that
  16. customwas used without further purification

Sources & evidence

ORD record
ord-6705c7bd090b417da4a16883e824c803
Source dataset
uspto-grants-2010_04
Patent number
US07691405B2

Reaction notes

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