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

HRID 1458353노트

반응식

HRID 1458353 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 57417360Sodium chloride; water용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-7e895af800934fbab7f031d69196731e
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05849764

반응 노트

불러오는 중…