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

HRID 1506986Notes

Reaction equation

HRID 1506986 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-f6f030d2052c4896b9c2be7026d45ec1
Source dataset
uspto-grants-2015_12
Patent number
US09221783B2

Reaction notes

Loading…