Water → HCID 58703546, compound

HRID 1179465Notes

Reaction equation

HRID 1179465 reaction equation
[Br:1][C:2]1[C:3]([O:14][CH2:15][O:16][CH3:17])=[C:4]([CH:7]=[C:8]([O:10][CH2:11][O:12][CH3:13])[CH:9]=1)[CH:5]=[O:6].[BH4-].[Na+].O.C([O-])(O)=O.[Na+]>CCO>[Br:1][C:2]1[C:3]([O:14][CH2:15][O:16][CH3:17])=[C:4]([CH2:5][OH:6])[CH:7]=[C:8]([O:10][CH2:11][O:12][CH3:13])[CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 58703550HCID 58703550, compound

Product 1

HCID 58703546HCID 58703546, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Treat a solution of 3-bromo-2,5-bis-methoxymethoxy benzaldehyde (9.40 g, 30.6 mmol) in EtOH (200 mL) with sodium borohydride (1.16 g, 30.6 mmol). Stir the reaction for 2 hours at ambient temperature and pour into H2O (200 mL) and saturated NaHCO3 (100 mL). Extract the H2O with EtOAc (3×100 mL) and wash the combined extracts with H2O (100 mL) and brine (50 mL) then dry (MgSO4) and filter. Concentrate the filtrate to afford the title product (9.31 g, 99%) as an oil. 1H NMR (CDCl3) δ 3.20 (t, J=6.9 Hz, 1H), 3.47 (s, 3H), 3.64 (s, 3H), 4.60 (d, J=6.9 Hz, 2H), 5.08 (s, 2H), 5.13 (s, 2H), 7.02 (d, J=2.9 Hz, 1H), 7.23 (d, J=2.9 Hz, 1H).

Workup

  1. customthe reaction for 2 hours at ambient temperature
  2. extractionExtract the H2O with EtOAc (3×100 mL)
  3. washwash the combined extracts with H2O (100 mL) and brine (50 mL)
  4. dry with materialthen dry (MgSO4)
  5. filtrationfilter
  6. concentrationConcentrate the filtrate

Sources & evidence

ORD record
ord-4e305721d5194b088a2cbdbb2f1e5d05
Source dataset
uspto-grants-2007_10
Patent number
US07279499B2

Reaction notes

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