Water → 3-[(tert-Butyldimethylsilyloxy)methyl]-6-formyl-1,2-dithiin

HRID 1079757

反応式

HRID 1079757 の反応式
[Si:1]([O:8][CH2:9][C:10]1[S:11][S:12][C:13]([CH2:16][OH:17])=[CH:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.O>C1COCC1>[Si:1]([O:8][CH2:9][C:10]1[S:11][S:12][C:13]([CH:16]=[O:17])=[CH:14][CH:15]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 962WaterHCID 159087TriacetoxyperiodinaneHCID 100628323-[(Tert-butyldimethylsilyloxy)methyl]-6-hydroxymethyl-1,2-dithiin

生成物 1

HCID 117788833-[(tert-Butyldimethylsilyloxy)methyl]-6-formyl-1,2-dithiin収率 94%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of 3-[(tert-butyldimethylsilyloxy)methyl]-6-(hydroxymethyl)-1,2-dithiin (U.S. Ser. No. 08/212,096) (600 mg, 2.07 mmol) in THF (25 mL) at 0° C. was added quickly the Dess-Martin periodinane reagent (1.20 g, 2.83 mmol) and the mixture was stirred at 0° C. for 30 min, then at room temperature for another 30 min. Upon completion of the reaction (monitored by TLC), 12 mL of H2O was added and the mixture was extracted with ether (3×). The combined organics washings were washed with H2O, sodium hydrogen carbonate (3%-soln.), brine, dried (Na2SO4) and evaporated. Flash chromatography (eluting with hexane/EtOAc 3/1) yielded 560 mg (94%) of the title aldehyde as a dark red, almost purple, crystalline compound.

後処理

  1. waitat room temperature for another 30 min
  2. additionwas added
  3. extractionthe mixture was extracted with ether (3×)
  4. washThe combined organics washings were washed with H2O, sodium hydrogen carbonate (3%-soln.), brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. washFlash chromatography (eluting with hexane/EtOAc 3/1)

出典と根拠

ORDレコード
ord-d08a7e6211b241ebadf1660bcca7aec2
出典データセット
uspto-grants-1996_12
特許番号
US05580897

関連ノート

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