Water → 1-Phenylcyclopentane-1-carbaldehyde

HRID 1427945노트

반응식

HRID 1427945 반응식
[C:1]1([C:7]2([CH2:12][OH:13])[CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.C(=O)(O)[O-].[Na+].O>C(Cl)Cl>[C:1]1([C:7]2([CH:12]=[O:13])[CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 123544(1-Phenylcyclopentyl)methanolHCID 159087TriacetoxyperiodinaneHCID 516892Sodium Bicarbonate

생성물 1

HCID 110951241-Phenylcyclopentane-1-carbaldehyde수율 81.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (1-Phenyl-cyclopentyl)-methanol (1.0 g, 5.7 mmol) in DCM (20 mL) was added Dess-Martin Periodine (6.8 mmol, 1.2 eq) and sodium bicarbonate (6.8 mmol, 1.2 eq) at 0° C. The reaction mixture stirred at this temperature for 2 h and allowed to warm up slowly to room temperature. After completion of the reaction, the mixture was poured into water (50 mL) and extracted with DCM (50 mL). The organic mixture was then dried over sodium sulfate and concentrated under reduced pressure to give 1-Phenyl-cyclopentanecarbaldehyde (812 mg) which was immediately used to synthesize title compound (14 mg) from Intermediate B (20 mg, 0.025 mmol) following general procedures D and B. LC-MS (m/z): 923.

후처리

  1. customAfter completion of the reaction
  2. extractionextracted with DCM (50 mL)
  3. dry with materialThe organic mixture was then dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-6fd1840555894a5f98ff9d4d4230ccae
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933222B2

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