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

HRID 1249806ノート

反応式

HRID 1249806 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
4 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-6c14fe3223974a08ba53c2ac24b2fbfa
出典データセット
uspto-grants-2002_01
特許番号
US06335353B1

反応ノート

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