Tetrahydrofuran → HCID 12376722, compound

HRID 1449328Notes

Reaction equation

HRID 1449328 reaction equation
C([N-]C(C)C)(C)C.[Li+].[CH3:9][O:10][C:11]1[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[C:25]([O:31][CH3:32])[C:12]=1[CH2:13][N:14]1[CH2:17][CH2:16][CH:15]1C(OC(C)(C)C)=O.[O:33]1CCCC1>>[CH3:9][O:10][C:11]1[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[C:25]([O:31][CH3:32])[C:12]=1[CH2:13][N:14]1[CH2:17][CH2:16][C:15]1=[O:33]

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 2724682Lithium diisopropylamideHCID 12376716HCID 12376716, compound

Product 1

HCID 12376722HCID 12376722, compoundYield 56%

Procedure

In a 50 ml round bottom 3-neck flask was prepared a solution of 1.2 mmol lithium diisopropylamide in ca. 10 ml tetrahydrofuran. To this clear, practically colorless solution cooled to -78°, was added 0.34 g (1 mmol) N-(2,4,6-trimethoxybenzyl)-2-carbo-tert-butoxyazetidine dissolved in 3 ml tetrahydrofuran. After stirring for 1 hour at this temperature, the golden-orange solution was silylated and photooxygenated in the usual manner. The resulting pink solution was then concentrated in vacuo and the residue applied to a 10×2 cm silica gel (Woelm) column. Elution with chloroform gave 0.14 g (56%) of pale yellow liquid, which by NMR analysis was greater than 90% pure: IR (liquid film) cm-1 1745, 1600, 1230, 1210, 1150, 1060, 1050, 950, 820; NMR (CDCl3) delta 6.09 (2H, s), 4.36 (2H, s), 3.79 (6H, s), 3.75 (3H, s), 2.98 (2H, t, J=4 Hz), 2.74 (2H, t, J=4 Hz).

Workup

  1. temperatureTo this clear, practically colorless solution cooled to -78°
  2. concentrationThe resulting pink solution was then concentrated in vacuo
  3. washElution with chloroform

Sources & evidence

ORD record
ord-3b88083b1f0f4ec5a4c548be4a8d3017
Source dataset
uspto-grants-1980_02
Patent number
US04190579

Reaction notes

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