N,N,N',N'-Tetramethylethylenediamine → HCID 18340685, compound

HRID 1369229Notes

Reaction equation

HRID 1369229 reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH3:6])=[O:5].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].CN(CCN(C)C)C.[CH3:25][O:26][C:27]1[CH:28]=[CH:29][C:30]2[CH2:36][C:35](=[O:37])[C:34]3[CH:38]=[CH:39][CH:40]=[CH:41][C:33]=3[O:32][C:31]=2[CH:42]=1>C1COCC1>[OH:37][C:35]1([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:34]2[CH:38]=[CH:39][CH:40]=[CH:41][C:33]=2[O:32][C:31]2[CH:42]=[C:27]([O:26][CH3:25])[CH:28]=[CH:29][C:30]=2[CH2:36]1

Participants

6

Reactant 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 8857Ethyl AcetateHCID 2733832Lithium HexamethyldisilazideHCID 19591954HCID 19591954, compound

Product 1

HCID 18340685HCID 18340685, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Anhydrous EtOAc (0.94 mL, 9.6 mmole) was added dropwise to a solution of lithium bis(trimethylsilyl)amide (1.0 M in THF, 7 mL, 7 mmole) in dry THF (7 mL) in a flame-dried flask at −78° C. under argon. After 0.5 hr, TMEDA (2.4 mL, 16 mmole) was added. After another 5 min, a solution of 3-methoxydibenzo[b,f]oxepin-10-one (760 mg, 3.2 mmole) in THF (2 mL) was added dropwise over 3 min. Additional dry THF (0.4 mL) was used in transfer. The reaction was stirred at −78° C. to −40° C. for 1 hr, then was quenched with saturated NH4Cl (10 mL). The mixture was wanned to RT and extracted with EtOAc. Drying (MgSO4), concentration, and flash chromatography on silica gel (10% EtOAc/hexanes) gave the title compound as a clear oil: 1H NMR (300 MHz, CDCl3) δ1.14-1.20 (t, 3 H), 1.21-1.30 (m, 1 H), 2.62-2.68 (dd, 1 H), 2.94-3.02 (dd, 1 H), 3.24-3.30 (dd, 1 H), 3.40-3.46 (dd, 1 H), 3.40-3.46 (dd, 1 H), 3.78 (s, 3 H), 4.08-4.18 (m, 2 H), 6.60-7.26 (m, 6 H), 7.64-7.68 (dd, 1 H).

Workup

  1. waitAfter another 5 min
  2. customwas quenched with saturated NH4Cl (10 mL)
  3. customwas wanned to RT
  4. extractionextracted with EtOAc
  5. customDrying
  6. concentration(MgSO4), concentration, and flash chromatography on silica gel (10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-8086550e25bb46c4a0685678430aef54
Source dataset
uspto-grants-2003_06
Patent number
US06576643B2

Reaction notes

Loading…