Hydrochloric Acid → HCID 25140393, compound

HRID 2272774Notes

Reaction equation

HRID 2272774 reaction equation
COC[O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH3:14])=[C:7]([O:15]COC)[C:6]=1[CH3:19].Cl.O>CO>[CH3:19][C:6]1[C:7]([OH:15])=[C:8]([O:11][CH2:12][CH2:13][CH3:14])[CH:9]=[CH:10][C:5]=1[OH:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 25140995HCID 25140995, compound

Product 1

HCID 25140393HCID 25140393, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 5b (580 mg, 2.15 mmol) in MeOH (17.9 mL) was treated dropwise with 3 M HCl (630 μL, 17.2 mmol), then heated to reflux for one hour. Water (20 mL) was added and the solution was extracted with EtOAc (3×20 mL). Combined organic fractions were washed with saturated aqueous NaCl, dried (Na2SO4), and concentrated to afford 6b as a red amorphous solid (387 mg, 99%). 1H NMR (CDCl3, 500 MHz) δ 6.51 (d, J=8.7 Hz, 1H), 6.21 (d, J=8.6 Hz, 1H), 5.74 (s, 1H), 4.36 (s, 1H), 3.87-3.85 (m, 2H), 2.09 (s, 3H), 1.75-1.71 (m, 2H), 0.96 (t, J=7.5 Hz, 3H); 13C NMR (CDCl3, 125 MHz) δ 147.5, 143.8, 139.0, 109.8, 108.4, 103.8, 70.2, 21.6, 9.5, 7.3; IR (film) νmax 3520, 3360, 2966, 2880, 2359, 2341, 1636, 1236, 1068, 785, 750 cm−1.

Workup

  1. temperatureheated
  2. temperatureto reflux for one hour
  3. extractionthe solution was extracted with EtOAc (3×20 mL)
  4. washCombined organic fractions were washed with saturated aqueous NaCl
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-22cace7234514a1ca3c806dce371d64d
Source dataset
uspto-grants-2015_09
Patent number
US09120774B2

Reaction notes

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