Tetrahydrofuran → HCID 58025809, compound

HRID 1694347Notes

Reaction equation

HRID 1694347 reaction equation
[Li]CCCC.CN(CCN(C)C)C.[CH:14]([Si:17]([CH:30]([CH3:32])[CH3:31])([CH:27]([CH3:29])[CH3:28])[O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][CH3:26])([CH3:16])[CH3:15].C1C[O:36][CH2:35]C1>CCOC(C)=O>[CH3:26][O:25][C:20]1[C:19]([O:18][Si:17]([CH:14]([CH3:16])[CH3:15])([CH:27]([CH3:29])[CH3:28])[CH:30]([CH3:32])[CH3:31])=[C:24]([CH:23]=[CH:22][CH:21]=1)[CH:35]=[O:36]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 22733856HCID 22733856, compoundHCID 178418339Butyllithium

Product 1

HCID 58025809HCID 58025809, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

nBuLi (2.5 M in hexanes) (36 mmol) is mixed with TMEDA (36 mmol) at 0° C. in a dry round bottom flask for 10 minutes. A solution of triisopropyl-(2-methoxy-phenoxy)-silane (24 mmol) in 25 mL of dry THF is added to the above mixture. The mixture is warmed up to room temperature in 2 hours by removal of the ice bath. The slightly yellow solution is then transferred to another dry flask containing dry 7.5 mL of DMF at room temperature. The mixture is stirred overnight. HCl (1 M) is added to the mixture to quench the reaction. The mixture is diluted with EtOAc (100 mL), washed with HCl (1 M) (2×100 mL) and brine (50 mL) and finally dried over anhydrous Na2 SO4. Purification is accomplished by silica flash chromatography (5% EtOAc/hexane) to yield 3-methoxy-2-triisopropylsilanyloxy-benzaldehyde as a colorless oil which needs to be stored at low temperatures: 1H NMR (400 MHz, CDCl3) δ 10.4 (s, 1H), 7.42 (dd, J1=7.7 Hz, J2=1.7 Hz, 1H), 7.67 (d, J1=8 Hz, J2=1.7 Hz, 1H), 7.04 (t, J=8.4 Hz, 1H), 3.96 (s, 3H), 1.26-1.35 (m, 3H), 1.13 (s, 9H), 1.12 (s, 9H). LC/MS (ES+): (M+1) 309.2. Rf=0.4 (5% EtOAc/hexane).

Workup

  1. customThe slightly yellow solution is then transferred to another dry flask
  2. additioncontaining
  3. dry with materialdry 7.5 mL of DMF at room temperature
  4. additionHCl (1 M) is added to the mixture
  5. customto quench
  6. customthe reaction
  7. washwashed with HCl (1 M) (2×100 mL) and brine (50 mL)
  8. customfinally dried over anhydrous Na2 SO4
  9. customPurification

Sources & evidence

ORD record
ord-2db540096e504deea3a0abda450e16d0
Source dataset
uspto-grants-2012_04
Patent number
US08158662B2

Reaction notes

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