Triphenylphosphine → HCID 20034926、化合物

HRID 231252

反応式

HRID 231252 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

HCID 20034926HCID 20034926、化合物収率 65%

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b270ecb836b944b4b0260c814845aa6b
出典データセット
uspto-grants-1989_07
特許番号
US04845231

関連ノート

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