4-Toluenesulfonyl chloride → (R)-2-(1-chloro-3-methylnaphthalen-2-yl)-2-hydroxyethyl 4-methylbenzenesulfonate

HRID 926214노트

반응식

HRID 926214 반응식
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([CH3:12])[C:3]=1[C@@H:13]([OH:16])[CH2:14][OH:15].C([Sn](=O)CCCC)CCC.[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1.CCN(CC)CC>C(Cl)Cl>[CH3:37][C:27]1[CH:32]=[CH:31][C:30]([S:33]([O:15][CH2:14][C@@H:13]([C:3]2[C:4]([CH3:12])=[CH:5][C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:2]=2[Cl:1])[OH:16])(=[O:35])=[O:34])=[CH:29][CH:28]=1

참가 물질

6

반응물 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 61221Dibutyltin oxideHCID 89677395(R)-1-(1-chloro-3-methylnaphthalen-2-yl)ethane-1,2-diol

생성물 1

HCID 89676690(R)-2-(1-chloro-3-methylnaphthalen-2-yl)-2-hydroxyethyl 4-methylbenzenesulfonate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of (R)-1-(1-chloro-3-methylnaphthalen-2-yl)ethane-1,2-diol (2.30 g, 9.74 mmol) in CH2Cl2 (97 mL), dibutyltinoxide (48.5 mg, 0.19 mmol), p-toluenesulfonyl chloride (2.08 g, 10.90 mmol), and Et3N (1.60 mL, 11.58 mmol) were added at room temperature). After stirring for 15 h, the reaction mixture was quenched with saturated aqueous NH4Cl, and then diluted with CH2Cl2. The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated and purified by flash column chromatography (silica gel, 0 to 100% ethyl acetate/hexanes) to give (R)-2-(1-chloro-3-methylnaphthalen-2-yl)-2-hydroxyethyl 4-methylbenzenesulfonate. 1H-NMR: 400 MHz, (CDCl3) δ 8.18 (d, J=8.8 Hz, 1H), 7.79 (d, J=8.4 Hz, 1H), 7.57-7.54 (m, 5H), 5.82 (t, J=5.6 Hz, 1H), 4.44 (dd, J=10.0, 6.8 Hz, 1H), 4.35 (dd, J=10.4, 5.6 Hz, 1H), 2.59 (s, 3H), 2.29 (s, 3H).

후처리

  1. customthe reaction mixture was quenched with saturated aqueous NH4Cl
  2. additiondiluted with CH2Cl2
  3. washThe organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash column chromatography (silica gel, 0 to 100% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-7c4f5e5121ba4c3b84d23c4eef26f316
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09284323B2

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