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

HRID 15289

반응식

HRID 15289 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

HCID 86598198Spiro(2.5)octane-6-carbaldehyde

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c30f4ecb7f5a47108df6f7c307355618
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732449B2

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