Acetone → HCID 16126089, compound

HRID 1716819Notes

Reaction equation

HRID 1716819 reaction equation
[Br:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([CH3:10])=[CH:8][CH3:9])[CH:6]=1.CC(C)=[O:13].C[N+]1([O-])CCOCC1.[OH2:23]>O=[Os](=O)(=O)=O>[Br:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([OH:13])([CH:8]([OH:23])[CH3:9])[CH3:10])[CH:6]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 82029Methyl morpholine oxideHCID 68509357HCID 68509357, compound

Product 1

HCID 16126089HCID 16126089, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

To a solution of 2-bromo-4-(1-methyl-propenyl)-thiophene (19.1 mmol, 4.15 g) in a cosolvent of acetone and water (15 mL/30 mL) was added at room temperature N-methyl morpholine oxide (NMO) (21.0 mmol, 4.92 g, 50% in H2O) and OsO4 (0.2 mmol, 1.27 g, 4% in H2O). The reaction mixture was stirred for 24 h at the temperature. After evaporation of acetone in vacuo, it was extracted with EtOAc (70 mL×4). The combined solution was washed with brine (70 mL), dried (MgSO4) and concentrated in vacuo. Chromatography on SiO2 (EtOAc/Hexanes, 2/3) gave 4.3 g (90%) of 2-(5-bromo-thiophen-3-yl)-butane-2,3-diol as an oil of isomeric mixture (major/minor, 8/1). Major isomer; 1H NMR (400 MHz, CDCl3) δ 7.10 (d, J=1.7 Hz, 1H), 7.02 (d, J=1.7 Hz, 1H), 3.81 (m, 1H), 2.54 (s, 1OH), 1.99 (d, J=5.7 Hz, 1OH), 1.53 (s, 3H), 1.04 (d, J=6.4 Hz, 3H). Minor isomer; 1H NMR (400 MHz, CDCl3) δ 7.14 (d, J=1.7 Hz, 1H), 7.04 (d, J=1.7 Hz, 1H), 3.90 (m, 1H), 2.58 (s, 1OH), 2.07 (d, J=4.0 Hz, 1OH), 1.46 (s, 3H), 1.13 (d, J=6.4 Hz, 3H).

Workup

  1. customAfter evaporation of acetone in vacuo, it
  2. extractionwas extracted with EtOAc (70 mL×4)
  3. washThe combined solution was washed with brine (70 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-21689a6d647e4563ab035561a934deb2
Source dataset
uspto-grants-2010_09
Patent number
US07803837B2

Reaction notes

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