Chloroform → 4-(4-Methoxyphenyl)morpholine

HRID 1014785

반응식

HRID 1014785 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.CC([O-])(C)C.[Na+].C(Cl)(Cl)Cl>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].C1(P(C2C=CC=CC=2)C2[C-](N(C)C)C=CC=2)C=CC=CC=1.[CH-]1C=CC=C1.[Fe+2]>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[CH:3][CH:4]=1

참가 물질

8

반응물 4

HCID 6212ChloroformHCID 77304-BromoanisoleHCID 8083MorpholineHCID 23676156Sodium t-butoxide

생성물 1

HCID 3898744-(4-Methoxyphenyl)morpholine수율 67%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1317290462-Diphenylphosphino-dimethylaminoferrocene촉매HCID 1140Toluene용매

실험 절차

According to General Procedure B, a mixture of 4-bromoanisole (63 μL, 0.50 mmol), morpholine (52 μL, 0.60 mmol), NaOt-Bu (67 mg, 0.70 mmol), Pd2(dba)3.CHCl3 (10 mg, 0.01 mmol), and 12f (8 mg, 0.02 mmol) in PhMe (2.5 mL) was heated, cooled and filtered. Evaporation of the solvent under reduced pressure and column chromatography of the pre-adsorbed crude material (2:50:48 Et3N/Et2O/hexane, silica gel) gave 52e (64 mg, 67%) as an off-white solid. 1H NMR (300 MHz, CDCl3) δ 6.92-6.84 (m, 4H), 3.86 (t, 4H, J=4.8 Hz), 3.77 (s, 3H), 3.06 (t, 4H, J=4.8 Hz); 13C NMR (75.5 MHz, CDCl3) δ 153.9, 145.5, 117.7, 114.4, 66.9, 55.5, 50.7.

후처리

  1. temperaturecooled
  2. filtrationfiltered
  3. customEvaporation of the solvent under reduced pressure and column chromatography of the pre-adsorbed crude material (2:50:48 Et3N/Et2O/hexane, silica gel)

출처 및 근거

ORD 기록
ord-7ff1dd8692fc4e1084019b4bdd77e28e
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07982064B2

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