Dimethyl Sulfide → HCID 14886217, compound

HRID 1987667Notes

Reaction equation

HRID 1987667 reaction equation
[Si:1]([O:8][CH2:9][C@H:10]1[C@H:15]([OH:16])[CH:14]=[CH:13][CH2:12][O:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:25])C=1.CSC>C(Cl)Cl>[Si:1]([O:8][CH2:9][CH:10]1[CH:15]([OH:16])[CH:14]2[CH:13]([O:25]2)[CH2:12][O:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 70297m-Chloroperbenzoic acidHCID 57723922HCID 57723922, compound

Product 1

HCID 14886217HCID 14886217, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C., stirred solution of trans-2-(tert-butyldimethylsilanyloxymethyl)-3,6-dihydro-2H-pyran-3-ol (0.110 g, 0.45 mmol) in CH2Cl2 (10 ml) was added m-CPBA (75%, 0.108 g, 1.08 mmol) and the mixture was stirred for 1 h at 0° C. Dimethyl sulfide (0.01 ml) was added and stirring was continued for 10 min. The solvent was removed in vacuo and the crude product was diluted with EtOAc (30 ml). The resulting solution was washed successively with saturated aqueous Na2CO3 (10 ml), water (10 ml×2) and brine (10 ml). The organic phase was dried over anhydrous Na2SO4. The solvent was removed in vacuo and the crude product was purified by flash chromatography (2540% EtOAc in hexane).

Workup

  1. stirringstirring
  2. waitwas continued for 10 min
  3. customThe solvent was removed in vacuo
  4. additionthe crude product was diluted with EtOAc (30 ml)
  5. washThe resulting solution was washed successively with saturated aqueous Na2CO3 (10 ml), water (10 ml×2) and brine (10 ml)
  6. dry with materialThe organic phase was dried over anhydrous Na2SO4
  7. customThe solvent was removed in vacuo
  8. customthe crude product was purified by flash chromatography (2540% EtOAc in hexane)

Sources & evidence

ORD record
ord-be482d398d744574986eeb3497505617
Source dataset
uspto-grants-2009_06
Patent number
US07550607B2

Reaction notes

Loading…