Imidazole → (S)-3-[(4-Iodomethyl-phenyl)-(tetrahydro-pyran-2-yloxy)-methyl]-benzonitrile

HRID 1818469ノート

反応式

HRID 1818469 の反応式
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]([O:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)[C:10]2[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=2)[C:13]#[N:14])=[CH:5][CH:4]=1.[I:25]I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[I:25][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]([O:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)[C:10]2[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=2)[C:13]#[N:14])=[CH:5][CH:4]=1

参加物

7

反応物 5

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 24477Sodium ThiosulfateHCID 573554673-{(S)-[4-(Hydroxymethyl)phenyl][(oxan-2-yl)oxy]methyl}benzonitrile

生成物 1

HCID 57884505(S)-3-[(4-Iodomethyl-phenyl)-(tetrahydro-pyran-2-yloxy)-methyl]-benzonitrile収率 82%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Add sequentially a solution of (S)-3-[(4-hydroxymethyl-phenyl)-(tetrahydro-pyran-2-yloxy)-methyl]-benzonitrile (2.0 g, 6.18 mmol) dichloromethane (20 ml) and a solution of iodine (1.72 g, 6.80 mmol) in dichloromethane (30 ml) to a cooled (0° C.) solution of triphenylphosphine (1.78 g, 6.80 mmol) and imidazole (635 mg, 9.33 mmol) in dichloromethane (20 ml). Allow to warm to room temperature, then stir for 1.5 hours. Pour the mixture into a cold (0° C.) solution of sodium thiosulfate (3.63 g, 23 mmol) in an ice/water mixture (250 g) and stir for 30 minutes. Extract the aqueous layer with dichloromethane (30 ml). Combine the organic extracts and wash with water, dry with sodium sulfate, filter and concentrate. Purify the crude product via silica chromatography eluting with 15:85 ethyl acetate:hexanes to give the title compound (2.19 g, 82%). MS (m/z). Parent ion not observed.

後処理

  1. stirringstir for 30 minutes
  2. extractionExtract the aqueous layer with dichloromethane (30 ml)
  3. washCombine the organic extracts and wash with water
  4. dry with materialdry with sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify the crude product via silica chromatography
  8. washeluting with 15:85 ethyl acetate

出典と根拠

ORDレコード
ord-fbb98eaf54d640ccae2d42aa5ee8705b
出典データセット
uspto-grants-2009_10
特許番号
US07598423B2

反応ノート

読み込み中…