Diisopropylamine → HCID 19822220, compound

HRID 1030399Notes

Reaction equation

HRID 1030399 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[CH3:13][O:14][CH2:15][O:16][C:17]1[C:18]([CH3:34])=[C:19]2[C:24](=[C:25]([CH3:28])[C:26]=1[CH3:27])[O:23][CH:22]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:21][CH2:20]2.[CH2:35](Br)[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42]>O1CCCC1.CCCCCC>[CH3:13][O:14][CH2:15][O:16][C:17]1[C:18]([CH3:34])=[C:19]2[C:24](=[C:25]([CH3:28])[C:26]=1[CH3:27])[O:23][C:22]([CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:21][CH2:20]2

Participants

7

Reactant 4

HCID 7912DiisopropylamineHCID 81401-BromooctaneHCID 19822166HCID 19822166, compoundHCID 178418339Butyllithium

Product 1

HCID 19822220HCID 19822220, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Conditions

Temperature
-60 °C

Procedure

7.8 ml of a hexane solution containing 1.62 mmole/ml of butyllithium were added dropwise to a mixture of 2 g of diisopropylamine and 80 ml of tetrahydrofuran under a nitrogen stream at a temperature from -60° to -50° C. The resulting mixture was then allowed to stand for 10 minutes at room temperature, after which about 10 ml of tetrahydrofuran containing 4 g of ethyl 6-methoxymethoxy-5,7,8-trimethylchroman-2-carboxylate (prepared as described in Preparation 11) were added and the mixture was stirred for 1 hour at -60° C. About 20 ml of tetrahydrofuran containing 5 g of octyl bromide were added, and the mixture was stirred for 1 hour at -60° C. and then for 1 hour at room temperature, after which it was heated for 1 hour at 50° C. The reaction mixture was then poured into ice-water and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, and the residue was subjected to silica gel column chromatography eluted with benzene, to give the title compound.

Workup

  1. stirringthe mixture was stirred for 1 hour at -60° C.
  2. waitfor 1 hour at room temperature
  3. temperatureafter which it was heated for 1 hour at 50° C
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed by distillation under reduced pressure
  8. washeluted with benzene

Sources & evidence

ORD record
ord-f2c40dc01dfc442ba29abdc6d1054e1e
Source dataset
uspto-grants-1992_04
Patent number
US05104888

Reaction notes

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