Allyl Alcohol → 3-(4-(Hydroxymethyl)phenyl)propanal

HRID 271635

反応式

HRID 271635 の反応式
[CH2:1]([OH:4])[CH:2]=[CH2:3].C([O-])(O)=O.[Na+].I[C:11]1[CH:18]=[CH:17][C:14]([CH2:15][OH:16])=[CH:13][CH:12]=1.CCOC(C)=O>O.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2].O>[OH:16][CH2:15][C:14]1[CH:17]=[CH:18][C:11]([CH2:3][CH2:2][CH:1]=[O:4])=[CH:12][CH:13]=1

参加物

9

反応物 4

HCID 7858Allyl AlcoholHCID 8857Ethyl AcetateHCID 290124-Iodobenzyl alcoholHCID 516892Sodium Bicarbonate

生成物 1

HCID 534252763-(4-(Hydroxymethyl)phenyl)propanal

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 16212273Tetrabutylammonium chloride hydrate触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

10.5 mL (152.8 mmol) allylalcohol, 18.8 g (62.2 mmol) Tetrabutylammonium chloride monohydrate, 12.8 g (152.8 mmol) NaHCO3 and 0.75 g (3.1 mmol) Pd(OAc)2 is added to a solution of 15.0 g (62.2 mmol) 4-iodobenzylalcohol in 100 mL DMF at RT under an N2 atmosphere and the reaction solution is heated to 60° C. for 3 h. The solvent is eliminated i.vac., the residue combined with 250 mL EtOAc and 80 mL water and suction filtered through a fibreglass filter. 80 mL NaCl solution are added to the filtrate, the phases are separated and the organic phase is dried over MgSO4. After the desiccant and solvent have been eliminated the residue is purified by column chromatography on silica gel (gradient: cyc/EtOAc 3:1 after cyc/EtOAc 1:1).

後処理

  1. filtrationfiltered through a fibreglass
  2. filtrationfilter
  3. addition80 mL NaCl solution are added to the filtrate
  4. customthe phases are separated
  5. dry with materialthe organic phase is dried over MgSO4
  6. customis purified by column chromatography on silica gel (gradient: cyc/EtOAc 3:1 after cyc/EtOAc 1:1)

出典と根拠

ORDレコード
ord-c091aec98fb744dc835629a691d3c1bb
出典データセット
uspto-grants-2008_11
特許番号
US07452911B2

関連ノート

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