Hydrochloric Acid → HCID 118061923, compound

HRID 920792Notes

Reaction equation

HRID 920792 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:16]([OH:18])=[O:17])[CH2:11][C:10]([O:14]C)(OC)[CH2:9]2)=[CH:4][CH:3]=1.Cl.[CH3:20]O>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:16]([O:18][CH3:20])=[O:17])[CH2:9][C:10](=[O:14])[CH2:11]2)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 118062710HCID 118062710, compound

Product 1

HCID 118061923HCID 118061923, compoundYield 80%

Procedure

To a stirred solution of Intermediate 308B (1.0 g, 3.93 mmol) in MeOH (15 mL) was added a concentrated aq. solution of HCl (5 mL) and the solution was stirred at RT for 12 h. The volatiles were removed under reduced pressure and the resulting residue was purified by silica gel chromatography (24 g REDISEP® column, eluting with 20% EtOAc in hexanes). Fractions containing the product were combined and evaporated to afford Intermediate 308C as a colorless oil (700 mg, 80%). 1H NMR (400 MHz, chloroform-d) δ ppm 7.45 (dd, J=8.94, 5.05 Hz, 2H), 7.09 (t, J=8.66 Hz, 2H), 3.89 (m, 2H), 3.71 (s, 3H), 3.57-3.72 (m, 2H).

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customthe resulting residue was purified by silica gel chromatography (24 g REDISEP® column, eluting with 20% EtOAc in hexanes)
  3. additionFractions containing the product
  4. customevaporated

Sources & evidence

ORD record
ord-db70c1a64d3b4ca78db40d98848e690a
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

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