Chloroform → 4-(4-Methoxyphenyl)morpholine

HRID 1014785

反応式

HRID 1014785 の反応式
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

参加物

8

反応物 4

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

生成物 1

HCID 3898744-(4-Methoxyphenyl)morpholine収率 67%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1317290462-Diphenylphosphino-dimethylaminoferrocene触媒HCID 1140Toluene溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-7ff1dd8692fc4e1084019b4bdd77e28e
出典データセット
uspto-grants-2011_07
特許番号
US07982064B2

関連ノート

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