Water → (1S)-1-(2-chloro-5-iodophenyl)ethane-1,2-diol

HRID 602060Notes

Reaction equation

HRID 602060 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][C:3]=1[CH:9]=[CH2:10].CC[C@H]1[C@H]2C[C@H]([C@H](OC3C4C(=CC=CC=4)C(O[C@H](C4C=CN=C5C=4C=C(OC)C=C5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=C([O:32]C)C=C4)N(CC2)C1.S([O-])([O-])=O.[Na+].[Na+].[OH2:75]>CC(O)(C)C.O.C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][C:3]=1[C@H:9]([OH:32])[CH2:10][OH:75]

Participants

7

Reactant 4

HCID 962WaterHCID 24437Sodium SulfiteHCID 510036741-((1R)-((2R,4R,5S)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)-4-((1R)-((2R,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)phthalazineHCID 574706061-Chloro-4-iodo-2-vinylbenzene

Product 1

HCID 57470607(1S)-1-(2-chloro-5-iodophenyl)ethane-1,2-diol

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 714019492-Methylpropan-2-ol--water (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

1-Chloro-4-iodo-2-vinylbenzene (2.43 g, 9.19 mmol) was dissolved in t-BuOH/H2O (1:1, 60 mL) and then cooled to 0° C. AD-mix-α (11 g) was slowly added. The reaction slowly warmed to rt overnight. Sodium sulfite (11 g) was added and the solution stirred at rt. After 3 h, H2O and CH2Cl2 were added and the organic layer isolated. The aqueous layer was washed with CH2Cl2 (3×) and then the combined organic extracts were combined, dried (Na2SO4), concentrated, and purified by Biotage chromatography (0%-100% EtOAc/hexanes) to afford 2.6 g of (1S)-1-(2-chloro-5-iodophenyl)ethane-1,2-diol as an oil that will solidify over time (95%). 1H NMR (400 MHz, chloroform-d) δ ppm 7.94 (d, J=2.27 Hz, 1 H) 7.55 (dd, J=8.34, 2.02 Hz, 1 H) 7.07 (d, J=8.34 Hz, 1 H) 5.17 (dd, J=7.58, 3.03 Hz, 1 H) 3.90 (dd, J=11.24, 3.16 Hz, 1 H) 3.54 (dd, J=11.24, 7.71 Hz, 1 H) 3.49 (s, 2 H).

Workup

  1. customThe reaction
  2. temperatureslowly warmed to rt overnight
  3. customthe organic layer isolated
  4. washThe aqueous layer was washed with CH2Cl2 (3×)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. custompurified by Biotage chromatography (0%-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-46901b69b89d41918febd22302ea0be4
Source dataset
uspto-grants-2011_03
Patent number
US07902394B2

Reaction notes

Loading…