Triethylsilane → 4-benzyl-6-[(5-bromo-2-chloro-phenyl)methyl]spiro[3H-1,4-benzoxazine-2,1'-cyclopropane]

HRID 1695843ノート

反応式

HRID 1695843 の反応式
[CH2:1]([N:8]1[C:15]2[CH:16]=[C:17]([CH:20]([C:22]3[CH:27]=[C:26]([Br:28])[CH:25]=[CH:24][C:23]=3[Cl:29])O)[CH:18]=[CH:19][C:14]=2[O:13][C:10]2([CH2:12][CH2:11]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([SiH](CC)CC)C.OS(C(F)(F)F)(=O)=O>FC(F)(F)C(O)=O>[CH2:1]([N:8]1[C:15]2[CH:16]=[C:17]([CH2:20][C:22]3[CH:27]=[C:26]([Br:28])[CH:25]=[CH:24][C:23]=3[Cl:29])[CH:18]=[CH:19][C:14]=2[O:13][C:10]2([CH2:12][CH2:11]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 12052TriethylsilaneHCID 62406Trifluoromethanesulfonic acidHCID 58340780(4-benzylspiro[3H-1,4-benzoxazine-2,1-cyclopropane]-6-yl)-(5-bromo-2-chloro-phenyl)methanol

生成物 1

HCID 583408334-benzyl-6-[(5-bromo-2-chloro-phenyl)methyl]spiro[3H-1,4-benzoxazine-2,1'-cyclopropane]収率 92.5%

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

反応条件

温度
50 °C

実験手順

To an ice cold solution of (4-benzylspiro[3H-1,4-benzoxazine-2,1′-cyclopropane]-6-yl)-(5-bromo-2-chloro-phenyl)methanol (780 mg, 1.7 mmol) in trifluoroacetic acid (4 mL) was added triethylsilane (1.32 mL, 8.3 mmol) followed by triflic acid (0.15 mL, 1.7 mmol). After heating the mixture for 15 min at 50° C., the reaction was cooled to room temperature. Trifluoroacetic acid was evaporated under reduced pressure, and the resulting residue was taken in saturated aq. sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was washed with water, brine, dried over sodium sulfate, and concentrated. The resulting residue was purified by silica gel column chromatography to furnish 4-benzyl-6-[(5-bromo-2-chloro-phenyl)methyl]spiro[3H-1,4-benzoxazine-2,1-cyclopropane] (715 mg).

後処理

  1. temperaturethe reaction was cooled to room temperature
  2. customTrifluoroacetic acid was evaporated under reduced pressure
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe resulting residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-ecc8d4ab3956491c9793b0c23cf6af61
出典データセット
uspto-grants-2012_04
特許番号
US08163704B2

反応ノート

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