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Hydrochloric Acid → 5-Dibutylamino-2-methoxy-benzaldehyde

HRID 1989813
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HRID 1989813 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([O:14][CH3:15])=[C:6]([CH:8]2[O:13]CCCO2)[CH:7]=1.[CH2:16]([NH:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH3:19].CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.Cl.[OH-].[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:16]([N:20]([CH2:21][CH2:22][CH2:23][CH3:24])[C:2]1[CH:3]=[CH:4][C:5]([O:14][CH3:15])=[C:6]([CH:7]=1)[CH:8]=[O:13])[CH2:17][CH2:18][CH3:19]
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참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 8148DibutylamineHCID 14798Sodium HydroxideHCID 80271Tri-o-tolylphosphineHCID 143787592-(5-Bromo-2-methoxyphenyl)-1,3-dioxane

생성물 1

HCID 858889065-Dibutylamino-2-methoxy-benzaldehyde수율 46%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매
HCID 1140Toluene용매

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온도
25 °C

실험 절차

2-(5-Bromo-2-methoxy-phenyl)-[1,3]dioxane (40 mmol), di-n-butylamine (48 mmol), Pd2(dba)3 (0.2 mmol, 1 mol % Pd), P(o-tol)3 (0.6 mmol) and Na-t-OBu (68 mmol) was stirred in degassed toluene (60 mL) at 80° C. for 18 h. The darkbrown mixture was poured into icecold hydrochloric acid (1 M, 200 mL) and stirred vigorously for 2 hours at 25° C. The solution was cooled to 0° C. and pH was adjusted to 9 using 6M NaOH(aq) and extracted with Et2O (4×100 mL). The organic phase was dried (Na2SO4) and the solvent was removed under reduced pressure. The resulting crude oil purified by flash chromatography using EtOAc/n-heptane (1:4, v/v) as eluent. The product was isolated as yellow oil in 46% yield.

후처리

  1. temperatureThe solution was cooled to 0° C.
  2. extractionextracted with Et2O (4×100 mL)
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. customthe solvent was removed under reduced pressure
  5. customThe resulting crude oil purified by flash chromatography
  6. customThe product was isolated as yellow oil in 46% yield

출처 및 근거

ORD 기록
ord-8261bab93a224a1980c3988478e40b97
출처 데이터셋
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07642367B2

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