Sulfuric Acid → HCID 69672858, compound

HRID 2406373Notes

Reaction equation

HRID 2406373 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH:5]([C:7]1[C:8]([I:21])=[C:9]2[C:16]3[CH2:17][CH2:18][CH2:19][CH2:20][C:15]=3[S:14][C:10]2=[N:11][C:12]=1[CH3:13])[OH:6])[CH3:2].C(O[C:27]([CH3:30])([CH3:29])[CH3:28])(=O)C.S(=O)(=O)(O)O>ClCCl>[CH2:1]([O:3][C:4](=[O:22])[CH:5]([C:7]1[C:8]([I:21])=[C:9]2[C:16]3[CH2:17][CH2:18][CH2:19][CH2:20][C:15]=3[S:14][C:10]2=[N:11][C:12]=1[CH3:13])[O:6][C:27]([CH3:30])([CH3:29])[CH3:28])[CH3:2]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 10908tert-Butyl acetateHCID 67606534HCID 67606534, compound

Product 1

HCID 69672858HCID 69672858, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl-2-[4-iodo-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridine-3-yl]-2-hydroxyacetate (3 g, 7 mmol) was taken up in 20 mL dichloromethane and tert-butyl acetate (20 mL, 170 mmol) and the mixture coiled to 3° C. in an ice/water bath. Concentrated sulphuric acid (1.14 mL, 21 mmol) was then added dropwise and the mixture allowed to warm to room temperature over 3 hours. The reaction was quenched by the addition of 100 mL of 1M NaOH and 100 mL water and the organic layer separated. The organics were washed with brine (100 mL), dried over MgSO4 and evaporated under reduced pressure. The residue was purified by flash chrmoatography using a gradient of EtOAc in heptane as eluant (0:100 to 30:70) to afford the title compound as a white solid (1.22 g, 36%). 1H NMR (400 MHz, CDCl3) δ 1.20 (t, 3H), 1.23 (s, 9H), 1.81-1.94 (m, 4H), 2.66 (s, 3H), 2.80-2.87 (m, 2H), 3.22-3.31 (m, 2H), 4.10-4.22 (m, 2H), 5.90 (s, 1H).

Workup

  1. customThe reaction was quenched by the addition of 100 mL of 1M NaOH and 100 mL water
  2. customthe organic layer separated
  3. washThe organics were washed with brine (100 mL)
  4. dry with materialdried over MgSO4
  5. customevaporated under reduced pressure
  6. customThe residue was purified by flash chrmoatography

Sources & evidence

ORD record
ord-b0f81f68dbec4c09a92aefbfed05daa7
Source dataset
uspto-grants-2014_08
Patent number
US08809363B2

Reaction notes

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