Dimethyl Sulfide → HCID 57723923, compound

HRID 1987668Notes

Reaction equation

HRID 1987668 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][C@H:10]1[C@@H:15]([OH:16])[C@H:14]2[C@H: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 57013861HCID 57013861, compound

Product 1

HCID 57723923HCID 57723923, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C., stirred solution of cis-2-(tert-butyldimethylsilanyloxymethyl)-3,6-dihydro-2H-pyran-3-ol (0.200 g, 0.91 mmol) in CH2Cl2 (15 ml) was added m-CPBA (75%, 0.46 g, 2.68 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 (25-40% EtOAc in hexane).

Workup

  1. stirringstirring
  2. customThe solvent was removed in vacuo
  3. additionthe crude product was diluted with EtOAc (30 ml)
  4. washThe resulting solution was washed successively with saturated aqueous Na2CO3 (10 ml), water (10 ml×2) and brine (10 ml)
  5. dry with materialThe organic phase was dried over anhydrous Na2SO4
  6. customThe solvent was removed in vacuo
  7. customthe crude product was purified by flash chromatography (25-40% EtOAc in hexane)

Sources & evidence

ORD record
ord-853380b854874a5c8b843b8fb9e90fb1
Source dataset
uspto-grants-2009_06
Patent number
US07550607B2

Reaction notes

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