Triphenylphosphine → HCID 20034926, 화합물

HRID 231252노트

반응식

HRID 231252 반응식
[OH:1][CH2:2][C:3]1([CH3:10])[CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=[O:9].O[C:12]1[CH:20]=[CH:19][C:15]([CH2:16][C:17]#[N:18])=[CH:14][CH:13]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1C=CC=CC=1.[OH-].[Na+]>[CH3:10][C:3]1([CH2:2][O:1][C:12]2[CH:20]=[CH:19][C:15]([CH2:16][C:17]#[N:18])=[CH:14][CH:13]=2)[CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=[O:9]

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 265484-Hydroxybenzyl cyanideHCID 5462977Diethyl azodicarboxylateHCID 113555322-Hydroxymethyl-2-methylcyclohexanone

생성물 1

HCID 20034926HCID 20034926, 화합물수율 65%

시약·촉매·용매 2

HCID 241Benzene용매HCID 14798Sodium Hydroxide용매

실험 절차

2-Hydroxymethyl-2-methylcyclohexanone [Pearson et al., J. Chem. Soc. Perkin I, 2774, 2778 (1980)] (3.7 g), 4-hydroxybenzyl cyanide (4.49 g) and triphenylphosphine (8.86 g) were dissolved in benzene (100 mL) and cooled in ice under a nitrogen atmosphere. Diethylazodicarboxylate (5.3 mL) was added dropwise and the mixture was allowed to warm to room temperature. The reaction was then refluxed overnight. After cooling to room temperature, the reaction mixture was diluted with 25% aqueous NaOH and extracted with benzene. The extracts were washed with saturated brine solution, dried over MgSO4, filtered and concentrated. The crude residue was chromatographed on SiO2, elution with dichloromethane to give 4.35 g (65% yield) of 2-methyl-2-[[4-(cyanomethyl)phenoxy]methyl]cyclohexanone as an amber oil.

후처리

  1. temperaturecooled in ice under a nitrogen atmosphere
  2. temperatureThe reaction was then refluxed overnight
  3. temperatureAfter cooling to room temperature
  4. extractionextracted with benzene
  5. washThe extracts were washed with saturated brine solution
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude residue was chromatographed on SiO2, elution with dichloromethane

출처 및 근거

ORD 기록
ord-b270ecb836b944b4b0260c814845aa6b
출처 데이터셋
uspto-grants-1989_07
특허 번호
US04845231

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