Diethyl Ether → 3-(Oxan-4-yl)propanal

HRID 253578노트

반응식

HRID 253578 반응식
[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][CH2:9][OH:10])[CH2:3][CH2:2]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.CCOCC.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][CH:9]=[O:10])[CH2:3][CH2:2]1

참가 물질

6

반응물 4

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 159087TriacetoxyperiodinaneHCID 222728913-(Oxan-4-yl)propan-1-ol

생성물 1

HCID 574496833-(Oxan-4-yl)propanal수율 83%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 3-(tetrahydro-pyran-4-yl)-propan-1-ol (11.8 g, 0.0825 mol) in CH2Cl2 (200 mL) was added Dess-Martin periodinane (70.27 g, 0.165 mol). The mixture was stirred at rt. When the reaction was complete, the solution was poured into Et2O (300 mL) and anhydrous K2CO3 (19.84 g, 0.165 mol) was added. The mixture was filtered. The filtrate was dried over Na2SO4, and concentrated under vacuum to give the crude product, which was purified by column chromatography to give 3-(tetrahydro-pyran-4-yl)-propionaldehyde (8.59 g, 83%). 1H NMR (CD3OD) δ 1.1-1.3 (m, 4H), 1.4-1.6 (m, 5H), 2.4-2.5 (t, 2H), 3.2-3.3 (m, 2H), 3.8-3.97 (m, 2H), 9.7-9.8 (s, 1H).

후처리

  1. additionwas added
  2. filtrationThe mixture was filtered
  3. dry with materialThe filtrate was dried over Na2SO4
  4. concentrationconcentrated under vacuum
  5. customto give the crude product, which
  6. customwas purified by column chromatography

출처 및 근거

ORD 기록
ord-ba07b43497c5406a8a380f9c2ec9510d
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07872028B2

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