Hydrochloric Acid → 3-((Tert-butyldimethylsilyl)oxy)propanal

HRID 1384052Notes

Reaction equation

HRID 1384052 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[O:11]([CH2:19][CH2:20][CH2:21][OH:22])[Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].C(N(CC)CC)C.Cl>C(Cl)Cl>[O:11]([CH2:19][CH2:20][CH:21]=[O:22])[Si:12]([C:15]([CH3:17])([CH3:18])[CH3:16])([CH3:14])[CH3:13]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 40777913-[(Tert-butyldimethylsilyl)oxy]propan-1-ol

Product 1

HCID 36623923-((Tert-butyldimethylsilyl)oxy)propanal

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

DMSO (24 mmol) is added to oxalyl chloride (11 mmol) in 40 mL of CH2Cl2 cooled to −78° C. After 15 minutes, alcohol 46 (10 mmol) is added. After an additional 15 minutes, triethylamine (50 mmol) is added. The mixture is allowed to warm to 0° C. and then poured into 0.1 M HCl (100 mL). The phases are separated, and the aqueous phase is extracted with ethyl acetate (2×100 mL). The organic phases are washed with water (100 mL), dried over anhydrous MgSO4, and concentrated in vacuo. The mixture is purified by flash chromatography to give the product as a colorless oil.

Workup

  1. waitAfter an additional 15 minutes
  2. temperatureto warm to 0° C.
  3. customThe phases are separated
  4. extractionthe aqueous phase is extracted with ethyl acetate (2×100 mL)
  5. washThe organic phases are washed with water (100 mL)
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe mixture is purified by flash chromatography

Sources & evidence

ORD record
ord-a99d66bef24646e7b36a58d2187dcce7
Source dataset
uspto-grants-2001_07
Patent number
US06258360B1

Reaction notes

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