4-Toluenesulfonyl chloride → HCID 86730908、化合物

HRID 587126ノート

反応式

HRID 587126 の反応式
[CH2:1]([O:8][CH:9]1[CH2:14][CH2:13][C:12]([CH2:17][OH:18])([C:15]#[N:16])[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.C(N(CC)CC)C.CCOC(C)=O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:29][C:19]1[CH:24]=[CH:23][C:22]([S:25]([O:18][CH2:17][C:12]2([C:15]#[N:16])[CH2:13][CH2:14][CH:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:10][CH2:11]2)(=[O:27])=[O:26])=[CH:21][CH:20]=1

参加物

7

反応物 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 71239740HCID 71239740、化合物

生成物 1

HCID 86730908HCID 86730908、化合物収率 36%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 4-(benzyloxy)-1-(hydroxymethyl)cyclohexanecarbonitrile (crude 770 mg, 1.0 equiv) in DCM (7 mL) was added p-toluenesulfonyl chloride (898 mg, 1.5 equiv), triethylamine (1.44 mL, 3.3 equiv) and DMAP (38 mg, 0.1 equiv). The solution was stirred at room temperature overnight. It was concentrated to give the residue. EtOAc (120 mL) was added. The organic solution was washed with saturated NaHCO3 (30 mL), H2O (30 mL) and HCl (1.0 N, 30 mL), brine (30 mL), dried over anhydrous Na2SO4 and then concentrated to give yellow solid which was purified by CombiFlash (24 g silica gel column, EtOAc/Hexane: 0-30%) to afford 450 mg (yield 36%) of (4-(benzyloxy)-1-cyanocyclohexyl)methyl 4-methylbenzenesulfonate as a white solid.

後処理

  1. concentrationIt was concentrated
  2. customto give the residue
  3. washThe organic solution was washed with saturated NaHCO3 (30 mL), H2O (30 mL) and HCl (1.0 N, 30 mL), brine (30 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customto give yellow solid which
  7. customwas purified by CombiFlash (24 g silica gel column, EtOAc/Hexane: 0-30%)

出典と根拠

ORDレコード
ord-13bd2df9edd24930b75ba90e0f78be1f
出典データセット
uspto-grants-2016_01
特許番号
US09226923B2

反応ノート

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