Chloride → 3-((Tert-butyldimethylsilyl)oxy)propanal

HRID 2287627Notes

Reaction equation

HRID 2287627 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[Si:11]([O:18][CH2:19][CH2:20][CH2:21][OH:22])([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].[Cl-].C(N(CC)CC)C>C(Cl)Cl.C(OCC)(=O)C>[Si:11]([O:18][CH2:19][CH2:20][CH:21]=[O:22])([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]

Participants

8

Reactant 5

HCID 312ChlorideHCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 40777913-[(Tert-butyldimethylsilyl)oxy]propan-1-ol

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of anhydrous dimethylsulfoxide (0.05 mole) in anhydrous methylene chloride (100 ml) cooled to 0° C. under nitrogen with stirring is added a solution of oxalyl chloride (0.05 mole) in anhydrous methylene chloride (100 ml). After stirring for 15 minutes, a solution of 1-tert-Butyldimethylsilyloxy-3-hydroxypropane (0.04 mole) inmethylene chloride (150 ml) is added over a period of 30 minutes. Then the reaction is quenched by adding triethyl amine (1 mole) slowly. The reaction mixture is diluted with ethyl acetate (200 ml), washed with water (75 ml), brine (75 ml), dried and concentrated. The product is used as such in the subsequent condensation step.

Workup

  1. stirringAfter stirring for 15 minutes
  2. customThen the reaction is quenched
  3. washwashed with water (75 ml), brine (75 ml)
  4. customdried
  5. concentrationconcentrated
  6. customsuch in the subsequent condensation step

Sources & evidence

ORD record
ord-59e1f88ee0c84ce8ab6bdffeb37fccb6
Source dataset
uspto-grants-2000_07
Patent number
US06084082

Reaction notes

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