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

HRID 1989813
ノート
印刷プレビュー

反応式

HRID 1989813 の反応式
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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

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

生成物 1

HCID 858889065-Dibutylamino-2-methoxy-benzaldehyde収率 46%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒
HCID 1140Toluene溶媒

反応条件

温度
25 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8261bab93a224a1980c3988478e40b97
出典データセット
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07642367B2

反応ノート

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