Hydrochloric Acid → HCID 17604266, compound

HRID 1836955Notes

Reaction equation

HRID 1836955 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][C:8]=1[CH:14]=[O:15])[CH3:2].[BH4-].[Na+].Cl>CCO>[Br:13][C:10]1[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:16])=[C:8]([CH2:14][OH:15])[CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 880259ethyl (4-bromo-2-formylphenoxy)acetateHCID 4311764Sodium borohydride

Product 1

HCID 17604266HCID 17604266, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
0 °C

Procedure

Ethyl (4-bromo-2-formylphenoxy)acetate (Example 1, 6.00 g, 21.0 mmol) in 200 mL abs EtOH was stirred under Ar and the mixture was cooled to 0° C. To this mixture was added NaBH4 (199 mg, 5.24 mmol) in portions. The reaction was stirred for 1 hour where TLC (25% EtOAc/hexanes) revealed complete reaction. At this point, 1 N HCl was added dropwise until slightly acidic and the EtOH was removed under reduced pressure. Water (100 mL) was added and the reaction transferred to a separatory funnel where it was extracted 3×100 mL with EtOAc. The combined organic layers were dried over Na2SO4, filtered, and removed in vacuo to provide the product (5.41 g, 89%) as a pure white solid. 1H-NMR (acetone-d6, δ): 1.24 (t, 3H), 4.21 (q, 2H), 4.76 (s, 2H), 4.85 (s, 2H), 6.98 (d, 1H), 7.46 (dd, 1H); 7.61 (d, 1H); LRMS (GC/MS/EI) 308 [M]+.

Workup

  1. customreaction
  2. customwas removed under reduced pressure
  3. additionWater (100 mL) was added
  4. customthe reaction transferred to a separatory funnel
  5. extractionwhere it was extracted 3×100 mL with EtOAc
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. customremoved in vacuo

Sources & evidence

ORD record
ord-9ad94752dfa04364819cbf1cfb1e3d4d
Source dataset
uspto-grants-2004_08
Patent number
US06780859B2

Reaction notes

Loading…