Hydrochloric Acid → 3-((Tert-butyldimethylsilyl)oxy)propanal

HRID 48087

반응식

HRID 48087 반응식
CS(C)=O.C(Cl)(=O)C(Cl)=O.[O:11]([CH2:19][CH2:20][CH2:21][OH:22])[Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].C(N(CC)CC)C.Cl>C(Cl)Cl>[O:11]([CH2:19][CH2:20][CH:21]=[O:22])[Si:12]([C:15]([CH3:17])([CH3:18])[CH3:16])([CH3:14])[CH3:13]

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 40777913-[(Tert-butyldimethylsilyl)oxy]propan-1-ol

생성물 1

HCID 36623923-((Tert-butyldimethylsilyl)oxy)propanal

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-78 °C

실험 절차

DMSO (24 mmol) is added to oxalyl chloride (11 mmol) in 40 mL of CH2Cl2 cooled to −78° C. After 15 minutes, alcohol 46 (10 mmol) is added. After an additional 15 minutes, triethylamine (50 mmol) is added. The mixture is allowed to warm to 0° C. and then poured into 0.1 M HCl (100 mL). The phases are separated, and the aqueous phase is extracted with ethyl acetate (2×100 mL). The organic phases are washed with water (100 mL), dried over anhydrous MgSO4, and concentrated in vacuo. The mixture is purified by flash chromatography to give the product as a colorless oil.

후처리

  1. waitAfter an additional 15 minutes
  2. temperatureto warm to 0° C.
  3. customThe phases are separated
  4. extractionthe aqueous phase is extracted with ethyl acetate (2×100 mL)
  5. washThe organic phases are washed with water (100 mL)
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe mixture is purified by flash chromatography

출처 및 근거

ORD 기록
ord-5c15f2fb99da45d49beebf1bfbf5498f
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06702705B1

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