Dimethyl Sulfoxide → 2-Formyl-3-benzyloxy-6-methyl-pyran-4(1H)-one

HRID 1634618노트

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HRID 1634618 반응식
[OH:1][CH2:2][C:3]1[O:4][C:5]([CH3:18])=[CH:6][C:7](=[O:17])[C:8]=1[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CS(C)=O.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH:2]([C:3]1[O:4][C:5]([CH3:18])=[CH:6][C:7](=[O:17])[C:8]=1[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:1]

참가 물질

5

반응물 3

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 111394092-hydroxymethyl-3-benzyloxy-6-methyl-pyran-4(1H)-one

생성물 1

HCID 120111872-Formyl-3-benzyloxy-6-methyl-pyran-4(1H)-one수율 87.7%

시약·촉매·용매 1

HCID 6212Chloroform용매

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온도
4 °C

실험 절차

To a solution of 2-hydroxymethyl-3-benzyloxy-6-methyl-pyran-4(1H)-one (5.28 g, 21.5 mmol, 1 eq) in 100 ml chloroform was added 27 ml of dimethyl sulfoxide and 18.5 ml of triethylamine and the reaction mixture was cooled with an ice-bath to an internal temperature of 3-5° C. Then sulfur trioxide pyridine complex (17.1 g 107 mmol, 5 eq) was added and the mixture was allowed to thaw to room temperature. After stirring for overnight at room temperature, the reaction mixture was washed with water (2×50 ml) and the organic phase was dried over Na2SO4, filtered and concentrated in vacuo to yield an organe oil. Further purification by column chromatography on silica gel (eluant: Et2O) furnished the pure product (4.6 g, 87.7%) as a white crystalline solid. m.p. 78-81° C.

후처리

  1. additionThen sulfur trioxide pyridine complex (17.1 g 107 mmol, 5 eq) was added
  2. customthaw to room temperature
  3. washthe reaction mixture was washed with water (2×50 ml)
  4. dry with materialthe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto yield an organe oil
  8. customFurther purification by column chromatography on silica gel (eluant: Et2O)

출처 및 근거

ORD 기록
ord-9b6b8ac6ab85415aafb03407a67d5464
출처 데이터셋
uspto-grants-2003_01
특허 번호
US06506911B2

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