Dimethyl Sulfoxide → 3-((Tert-butyldimethylsilyl)oxy)propanal

HRID 742546Notes

Reaction equation

HRID 742546 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].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

7

Reactant 4

HCID 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 6344DichloromethaneSolvent3×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) in methylene 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-b0b17e467fc64db783105eeb2a0c2330
Source dataset
uspto-grants-1996_09
Patent number
US05554746

Reaction notes

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