Hydrochloric Acid → HCID 67513093, compound

HRID 1508547Notes

Reaction equation

HRID 1508547 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][OH:14])=[CH:7][C:6]=1[I:15].CC(C)([O-])C.[K+].Cl>C1COCC1>[I:15][C:6]1[CH:7]=[C:8]([CH2:11][CH2:12][CH2:13][OH:14])[CH:9]=[CH:10][C:5]=1[O:4][CH:3]=[CH2:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 67512930HCID 67512930, compound

Product 1

HCID 67513093HCID 67513093, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. solution of 3-[4-(2-chloroethoxy)-3-iodophenyl]propan-1-ol (Step B) (1.00 g, 2.94 mmol) in THF (10 ml) was added potassium tert-butoxide (1M in THF) (6.61 ml, 6.61 mmol). The resulting solution was warmed to RT (turned cloudy) and stirred under nitrogen for 3 hours. Dilute HCl was added to the mixture and extracted 2 times with ethyl acetate. The combined organics were washed with brine and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with EtOAc in hexanes to afford the title compound. 1H NMR (500 MHz, CD3OD): δ 7.66 (s, 1H); 7.23-7.13 (m, 1H); 6.96-6.88 (m, 1H); 6.66 (ddd, J=28.0, 13.7, 6.2 Hz, 1H); 4.64-4.60 (m, 1H); 4.43 (dd, J=6.1, 1.6 Hz, 1H); 3.54 (t, J=6.4 2H); 2.62 (t, J=7.6 Hz, 3H); 1.81-1.74 (m, 3H).

Workup

  1. extractionextracted 2 times with ethyl acetate
  2. washThe combined organics were washed with brine
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by flash column chromatography on silica gel
  5. washeluting with EtOAc in hexanes

Sources & evidence

ORD record
ord-bb7409a5d95f4f2bb8a820582dc86b8f
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

Loading…