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

HRID 1506986ノート

反応式

HRID 1506986 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-f6f030d2052c4896b9c2be7026d45ec1
出典データセット
uspto-grants-2015_12
特許番号
US09221783B2

反応ノート

読み込み中…