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

HRID 271635

반응식

HRID 271635 반응식
[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

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 16212273Tetrabutylammonium chloride hydrate촉매HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-c091aec98fb744dc835629a691d3c1bb
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452911B2

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