Sodium borohydride → (4-Methoxy-5-(2-trimethylsilanyl-ethoxymethoxy)-2-trimethylstannanyl-phenyl]-methanol

HRID 2181541Notes

Reaction equation

HRID 2181541 reaction equation
[CH3:1][O:2][C:3]1[C:10]([O:11][CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])=[CH:9][C:6]([CH:7]=[O:8])=[C:5]([Sn:20]([CH3:23])([CH3:22])[CH3:21])[CH:4]=1.[BH4-].[Na+]>CO.O>[CH3:1][O:2][C:3]1[C:10]([O:11][CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:17])([CH3:18])[CH3:19])=[CH:9][C:6]([CH2:7][OH:8])=[C:5]([Sn:20]([CH3:21])([CH3:23])[CH3:22])[CH:4]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 218774404-Methoxy-5-(2-trimethylsilanyl-ethoxymethoxy)-2-trimethylstannanyl-benzaldehyde

Product 1

HCID 21877510(4-Methoxy-5-(2-trimethylsilanyl-ethoxymethoxy)-2-trimethylstannanyl-phenyl]-methanolYield 91.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Preparation of (4-[methoxy-5-(2-trimethylsilanyl-ethoxymethoxy)-2-trimethylstannanyl-phenyl]-methanol: 4-Methoxy-5-(2-trimethylsilanyl-ethoxymethoxy)-2-trimethylstannanyl-benzaldehyde (2.36 g, 5.3 mmol) was stirred in MeOH (30 mL) at 0° C. Sodium borohydride (400 mg, 10.6 mmol) was added, and the reaction stirred for 1 h. The solution was diluted with H2O (60 mL), and extracted with EtOAc (2×50 mL). Organics were washed with brine (50 mL), dried (Na2SO4), and concentrated in vacuo to give 2.16 g (91%) of (4-methoxy-5-(2-trimethylsilanyl-ethoxymethoxy)-2-trimethylstannanyl-phenyl]-methanol as a clear oil. 1H NMR (300 MHz, CDCl3) δ 7.18 (t, 1H, J=6.9 Hz), 7.03 (t, 1H, J=9.3 Hz), 5.27 (s, 2H), 4.58-4.63 (m, 2H), 3.89 (s, 3H), 3.80 (t, 2H, J=8.4 Hz), 1.53 (t, 1H, J=6.0 Hz), 0.96 (t, 2H, J=8.4 Hz), 0.31 (t, 9H, J=27.3 Hz), 0.01 (s, 9H).

Workup

  1. extractionextracted with EtOAc (2×50 mL)
  2. washOrganics were washed with brine (50 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-30191825984e47cf96428e4c8467e362
Source dataset
uspto-grants-2005_05
Patent number
US06891044B2

Reaction notes

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