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

HRID 1079757

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HRID 1079757 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d08a7e6211b241ebadf1660bcca7aec2
출처 데이터셋
uspto-grants-1996_12
특허 번호
US05580897

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