2,2-Dimethoxypropane → (+/-)-4-(Benzyloxymethyl)-5-(2-chlorophenyl)-2,2-dimethyl-1,3-dioxolane

HRID 1506986노트

반응식

HRID 1506986 반응식
[CH2:1]([O:8][CH2:9][CH:10]([OH:20])[CH:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[Cl:19])[OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]1(C)[CH:26]=CC(S(Cl)(=O)=O)=C[CH:22]=1.COC(OC)(C)C>C(Cl)Cl>[CH2:1]([O:8][CH2:9][CH:10]1[CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])[O:12][C:21]([CH3:26])([CH3:22])[O:20]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 64952,2-DimethoxypropaneHCID 73974-Toluenesulfonyl chlorideHCID 90026408(+/-)-3-(Benzyloxy)-1-(2-chlorophenyl)propane-1,2-diol

생성물 1

HCID 90027002(+/-)-4-(Benzyloxymethyl)-5-(2-chlorophenyl)-2,2-dimethyl-1,3-dioxolane수율 8,262.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (±)-3-(benzyloxy)-1-(2-chlorophenyl)propane-1,2-diol (Preparation example 370, 2.4 g, 8.2 mmole) in CH2Cl2 (40 mL) was added p-toluenesulfonyl chloride (15.2 g, 0.08 mmole), and dimethoxypropan (8.4 mL, 9.84 mmole) at 0° C. sequently. The mixture was stirred for 1.5 hr at room temperature. The TLC showed complete consumption of SM. The reaction mixture was quenched with H2O then extracted with EtOAc. The aqueous layer was extracted with EtOAc and separated. The combined organic layer was washed with H2O, then dried over MgSO4 and evaporated under reduced pressure. The crude compound was purified by silica ge column to produce the title compound (2.2 g, 75˜90%).

후처리

  1. customconsumption of SM
  2. customThe reaction mixture was quenched with H2O
  3. extractionthen extracted with EtOAc
  4. extractionThe aqueous layer was extracted with EtOAc
  5. customseparated
  6. washThe combined organic layer was washed with H2O
  7. dry with materialdried over MgSO4
  8. customevaporated under reduced pressure
  9. customThe crude compound was purified by silica ge column

출처 및 근거

ORD 기록
ord-f6f030d2052c4896b9c2be7026d45ec1
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221783B2

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