Sodium borohydride → HCID 22486246, compound

HRID 2181539Notes

Reaction equation

HRID 2181539 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([O:14][CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])=[CH:8][C:5]=1[CH:6]=[O:7]>CO.O>[Br:3][C:4]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([O:14][CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:21])([CH3:20])[CH3:22])=[CH:8][C:5]=1[CH2:6][OH:7]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 21877258HCID 21877258, compound

Product 1

HCID 22486246HCID 22486246, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Sodium borohydride (275 mg, 7.2 mmol) was added in portions over 10 min to a solution of 2-bromo-4-methoxy-5-(2-trimethylsilanyl-ethoxymethoxy)-benzaldehyde (1.3 g, 3.6 mmol) in MeOH (20 mL) at 0° C. After 30 min, the reaction was diluted with H2O (40 mL) and extracted with EtOAc (2×30 mL). Organics were washed with brine (30 mL), dried (Na2SO4) and concentrated in vacuo to give 1.31 g of (2-bromo-4-methoxy-5-(2-trimethylsilanyl-ethoxymethoxy)-phenyl]-methanol as a clear oil. 1H NMR (300 MHz, CDCl3) δ 7.29 (s, 1H), 7.05 (s, 1H), 5.27 (s, 2H), 4.66 (d, 2H, J=6.6 Hz), 3.87 (s, 3H), 3.79 (t, 2H, J=8.4 Hz), 1.92 (t, 1H, J=6.6 Hz), 0.96 (t, 2H, J=8.4 Hz), 0.01 (s, 9H).

Workup

  1. extractionextracted with EtOAc (2×30 mL)
  2. washOrganics were washed with brine (30 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ea094d9d52b24b9ebbfeab0864eb01e4
Source dataset
uspto-grants-2005_05
Patent number
US06891044B2

Reaction notes

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