Diethyl Ether → 3-(Oxan-4-yl)propanal

HRID 253578ノート

反応式

HRID 253578 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 574496833-(Oxan-4-yl)propanal収率 83%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ba07b43497c5406a8a380f9c2ec9510d
出典データセット
uspto-grants-2011_01
特許番号
US07872028B2

反応ノート

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