Water → (r)-1-(6-Choro-pyridin-3-yl)-ethane-1,2-diol

HRID 1059082Notes

Reaction equation

HRID 1059082 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH2:9])=[CH:4][N:3]=1.S([O-])([O-])=[O:11].[Na+].[Na+].[OH2:16]>C(O)(C)(C)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C@@H:8]([OH:11])[CH2:9][OH:16])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24437Sodium SulfiteHCID 118154432-Chloro-5-vinyl-pyridine

Product 1

HCID 11182911(r)-1-(6-Choro-pyridin-3-yl)-ethane-1,2-diol

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Procedure

To a cooled 5° C., stirred slurry of AD_Mix-β® (150 g) in water (530 mL) and t-butanol (450 mL) was added a solution of 2-chloro-5-vinylpyridine (15.0 grams) in t-butanol (80 mL). After 6 hours, solid sodium sulfite (160 grams) was added and the resulting slurry was allowed to stir at ambient temperature for 30 minutes. This mixture was extracted with ethyl acetate (3 times), the combined organic layers were washed with saturated aqueous brine, dried over sodium sulfate and concentrated in vacuo. The resulting oil was chromatographed on 500 grams of silica gel eluting with a gradient of ethyl acetate (70-80%)/hexanes to afford the title compound as a colorless oil, 17.8 grams 1H NMR (400 MHz, CDCl3): δ=8.35 (s, 1H); 7.71 (d, 1H); 7.30 (d, 1H); 4.85 (dd, 1H); 3.63 (dd, 1H).

Workup

  1. extractionThis mixture was extracted with ethyl acetate (3 times)
  2. washthe combined organic layers were washed with saturated aqueous brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resulting oil was chromatographed on 500 grams of silica gel eluting with a gradient of ethyl acetate (70-80%)/hexanes

Sources & evidence

ORD record
ord-a5fe611ab05648b98ecc426627aabe7c
Source dataset
uspto-grants-2003_02
Patent number
US06518431B2

Reaction notes

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