Dimethyl Sulfoxide → 2,2-Dimethyl-3-((tetrahydro-2H-pyran-2-yl)oxy)propanal

HRID 1046438

반응식

HRID 1046438 반응식
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH3:11][C:12]([CH3:23])([CH2:15][O:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][O:18]1)[CH2:13][OH:14].C(N(CC)CC)C.[NH4+].[Cl-]>ClCCl>[CH3:11][C:12]([CH3:23])([CH2:15][O:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][O:18]1)[CH:13]=[O:14]

참가 물질

7

반응물 5

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 65578Oxalyl chlorideHCID 158113652,2-Dimethyl-3-(tetrahydro-pyran-2-yloxy)-propan-1-ol

생성물 1

HCID 132764582,2-Dimethyl-3-((tetrahydro-2H-pyran-2-yl)oxy)propanal수율 97.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-78 °C

실험 절차

DMSO (2.69 mL, 50.97 mmol) was added dropwise to a solution of oxalyl chloride (2.87 mL, 33.98 mmol) in dichloromethane (85.0 mL) at −78° C. After several minutes, neat 2,2-dimethyl-3-(tetrahydro-pyran-2-yloxy)-propan-1-ol (3.2 g, 16.99 mmol) was added dropwise and after stirring for 1 h at −78° C., triethylamine (9.5 mL, 68.0 mmol) was added. The reaction was allowed to warm to room temperature and stirred for 30 min. Sat. NH4Cl was added and the organic layer was separated. The aqueous layer was extracted with ethyl acetate and washed with brine. The organic layers were combined, dried over Na2SO4 and concentrated to give a pale liquid. The crude liquid was passed through a short silica gel column and eluted with 50% ethyl acetate in hexanes to provide 2,2-dimethyl-3-(tetrahydro-pyran-2-yloxy)-propionaldehyde (3.09 g, 97%) as a pale liquid after removal of solvents under reduced pressure.

후처리

  1. waitAfter several minutes
  2. temperatureto warm to room temperature
  3. stirringstirred for 30 min
  4. customthe organic layer was separated
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customto give a pale liquid
  10. washeluted with 50% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-20da1a9063e842bd9d058a0d784b622f
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569302B2

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