Dimethyl Sulfide → HCID 57672469, compound

HRID 2101808Notes

Reaction equation

HRID 2101808 reaction equation
[CH3:1][C@@H:2]([C@H:7]([C:11]1[CH:16]=[CH:15][C:14]([O:17]CC2C=CC=CC=2)=[CH:13][CH:12]=1)/[CH:8]=[CH:9]\[CH3:10])[C:3]([O:5][CH3:6])=[O:4].ClB(Cl)Cl.CSC.C(=O)(O)[O-].[Na+]>C(Cl)Cl.CCOC(C)=O>[OH:17][C:14]1[CH:13]=[CH:12][C:11]([C@H:7](/[CH:8]=[CH:9]\[CH3:10])[C@H:2]([CH3:1])[C:3]([O:5][CH3:6])=[O:4])=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 1068Dimethyl SulfideHCID 25135Boron TrichlorideHCID 516892Sodium BicarbonateHCID 57672450HCID 57672450, compound

Product 1

HCID 57672469HCID 57672469, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A reaction mixture of (2S,3R,Z)-methyl 3-(4-(benzyloxy)phenyl)-2-methylhex-4-enoate 41.2 (0.45 g, 1.4 mmol), trichloroborane (0.99 g, 8.5 mmol) and dimethylsulfane (0.53 g, 8.5 mmol) in DCM (10.0 mL) was stirred at 0° C. for 5 minutes and then at room temperature for 7 hours. A saturated solution of sodium bicarbonate was added slowly at 0° C. to reach a pH of 6.5. EtOAc was added, and the organic layer was washed with brine (2×25 mL) and dried with Na2SO4. The product was purified by reverse phase HPLC to give the title compound (41.3) as the major product in a ratio of 95:5. 1H NMR (500 MHz, CDCl3) δ ppm 1.21 (d, J=6.85 Hz, 3H) 2.77 (td, J=6.97, 2.93 Hz, 1H) 3.47-3.50 (m, 3H) 3.82 (m, 1H) 5.50-5.65 (m, 2H) 6.71-6.80 (m, 2H) 7.08 (d, J=8.56 Hz, 2H). MS ESI (pos.) m/e: 235.1 (M+H)+.

Workup

  1. waitat room temperature for 7 hours
  2. washthe organic layer was washed with brine (2×25 mL)
  3. dry with materialdried with Na2SO4
  4. customThe product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-93282b9d1e024acfa6d9f0ddf82856a2
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

Loading…