Dimethyl Sulfoxide → 4-(3-Methylisoxazol-5-yl)-butyraldehyde

HRID 1458353Notes

Reaction equation

HRID 1458353 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][C:12]1[CH:16]=[C:15]([CH2:17][CH2:18][CH2:19][CH2:20][OH:21])[O:14][N:13]=1.C(N(CC)CC)C>C(Cl)Cl.[Cl-].[Na+].O>[CH3:11][C:12]1[CH:16]=[C:15]([CH2:17][CH2:18][CH2:19][CH:20]=[O:21])[O:14][N:13]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 221009164-(3-Methylisoxazol-5-yl)butan-1-ol

Product 1

HCID 221009094-(3-Methylisoxazol-5-yl)-butyraldehydeYield 48.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of oxalyl chloride (0.40 mL of a 2M solution in methylene chloride in 2 mL dry methylene chloride) at -78° C. was added a solution of methyl sulfoxide (126 mg in 1 mL methylene chloride) and the mixture stirred at low temperature for 3 minutes. A solution of 4-(3-methylisoxazol-5-yl)-butan-1-ol (100 mg in 1 mL methylene chloride) was added and the reaction allowed to proceed for 15 minutes after which time 0.67 mL triethylamine were added and the mixture allowed to warm to room temperature. After 30 minutes brine was added and the mixture extracted with methylene chloride. The organic portion was dried over sodium sulfate and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (ethyl acetate:hexane, 1:1) gave the title compound (48 mg).

Workup

  1. waitto proceed for 15 minutes
  2. extractionthe mixture extracted with methylene chloride
  3. dry with materialThe organic portion was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customPurification of the residue by flash chromatography on silica gel (ethyl acetate:hexane, 1:1)

Sources & evidence

ORD record
ord-7e895af800934fbab7f031d69196731e
Source dataset
uspto-grants-1998_12
Patent number
US05849764

Reaction notes

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