4-Toluenesulfonyl chloride → HCID 86730908, 화합물

HRID 587126노트

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HRID 587126 반응식
[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

참가 물질

7

반응물 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 71239740HCID 71239740, 화합물

생성물 1

HCID 86730908HCID 86730908, 화합물수율 36%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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%)

출처 및 근거

ORD 기록
ord-13bd2df9edd24930b75ba90e0f78be1f
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09226923B2

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