Dimethylformamide → 6-(Tert-butyldimethylsilyloxy)-2-naphthaldehyde

HRID 713925Notes

Reaction equation

HRID 713925 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH:6]=[CH:5]2.[Li]CCCC.CN([CH:28]=[O:29])C>C1COCC1>[Si:13]([O:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[CH:3]=[C:2]([CH:28]=[O:29])[CH:11]=[CH:10]2)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 134730832-Bromo-6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]naphthaleneHCID 178418339Butyllithium

Product 1

HCID 212993096-(Tert-butyldimethylsilyloxy)-2-naphthaldehydeYield 76.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (6-bromonaphthalen-2-yloxy)(tert-butyl)dimethylsilane (4 g, 0.01 mol, 1.0 equiv) in dry THF (30 mL) at −78° C. under N2 atmosphere was added n-BuLi (2.5 M, 12 mL, 3.0 equiv) dropwise and stirred for 30 min. Then DMF (7.3 g, 0.1 mol, 10 equiv) was added and stirred for another 1 h, then quenched with water, extracted with ethyl acetate and washed with brine, dried over Na2SO4 and concentrated to obtain crude product. The crude product was purified by silica gel chromatography (PE:EA=20:1) to give compound the title compound (2.2 g, 64%) as a yellow liquid. ESI-MS (M+1)+: 287.0. 1H NMR (400 MHz, CDCl3) δ: 10.10 (s, 1H), 8.26 (s, 1H), 7.91-7.88 (m, 2H), 7.78-7.76 (m, 1H), 7.24-7.167 (m, 2H), 1.03 (s, 9H), 0.28 (s, 6H).

Workup

  1. stirringstirred for another 1 h
  2. customquenched with water
  3. extractionextracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customto obtain crude product
  8. customThe crude product was purified by silica gel chromatography (PE:EA=20:1)

Sources & evidence

ORD record
ord-4f4fa2258b9341519aec33261700589e
Source dataset
uspto-grants-2015_11
Patent number
US09186367B2

Reaction notes

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