Cornforth reagent → Spiro(2.5)octane-6-carbaldehyde

HRID 15289

反応式

HRID 15289 の反応式
[CH2:1]1[C:3]2([CH2:8][CH2:7][CH:6]([CH2:9][OH:10])[CH2:5][CH2:4]2)[CH2:2]1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH2:2]1[C:3]2([CH2:8][CH2:7][CH:6]([CH:9]=[O:10])[CH2:5][CH2:4]2)[CH2:1]1

参加物

4

反応物 2

HCID 2724130Cornforth reagentHCID 53487089(Spiro(2.5)octan-6-yl)methanol

生成物 1

HCID 86598198Spiro(2.5)octane-6-carbaldehyde

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Spiro[2.5]oct-6-yl-methanol (2.57 g, 18.3 mmol, 1.0 eq.) was dissolved in CH2Cl2 (30 mL) and placed in a ice-water bath at 0° C. Pyridinium dichromate (PCC) (7.9 g, 36.6 mmol, 2.0 eq.) was added and the reaction warmed to room temperature for 4 hours with stirring. The crude reaction was filtered through a Celite pad and washed with CH2Cl2 and evaporated. The crude material was dissolved in diethyl ether and filtered through Celite, washing with diethyl ether several times. Evaporated solvent to provide Spiro[2.5]octane-6-carbaldehyde as a brown oil (2.98 g, quantitative) that was used directly. 1H NMR (CHCl3, 400 MHz) δ 0.17-0.27 (m, 4H), 0.88-0.91 (m, 2H), 1.09-1.25 (m, 2H), 1.52-1.54 (m, 2H), 1.69-1.75 (m, 3H), 9.44 (d, 1H, J=1.2 Hz).

後処理

  1. customplaced in a ice-water bath at 0° C
  2. customThe crude reaction
  3. filtrationwas filtered through a Celite pad
  4. washwashed with CH2Cl2
  5. customevaporated
  6. dissolutionThe crude material was dissolved in diethyl ether
  7. filtrationfiltered through Celite
  8. washwashing with diethyl ether several times

出典と根拠

ORDレコード
ord-c30f4ecb7f5a47108df6f7c307355618
出典データセット
uspto-grants-2010_06
特許番号
US07732449B2

関連ノート

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