Diisopropylamine → HCID 20366327, compound

HRID 616851Notes

Reaction equation

HRID 616851 reaction equation
[CH:1]([NH:4]C(C)C)(C)C.C([Li])CCC.C(O[CH:16]([O:18][CH:19]([O:21][CH2:22][CH3:23])[CH3:20])[CH3:17])C.Br[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32].[O:36]1C[CH2:39][CH2:38][CH2:37]1>CCCCCC.CN(C)P(=O)(N(C)C)N(C)C>[C:31]([CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][C:16]([O:18][CH:19]([O:21][CH2:22][CH3:23])[CH3:20])([C:17]1[O:36][CH:37]=[CH:38][CH:39]=1)[C:1]#[N:4])([O:33][CH2:34][CH3:35])=[O:32]

Participants

8

Reactant 5

HCID 7912DiisopropylamineHCID 8028TetrahydrofuranHCID 122490Ethyl 7-bromoheptanoateHCID 104646311-Ethoxyethyl etherHCID 178418339Butyllithium

Product 1

HCID 20366327HCID 20366327, compound

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
-5 °C

Procedure

To a stirred solution of 84 ml of diisopropylamine in 280 ml of dry tetrahydrofuran (THF) is added 260 ml of 2.3M n-butyllithium in hexane during 30 min. at 0°-5° C. After stirring for 25 min. at -5° C. the solution is cooled to -75° C. and treated with a solution of 113g (0.58 mol) of 1-ethoxyethyl ether of furfural cyanohydrin (Example 1) in 115 ml of hexamethylphosphoric triamide during 45 min. at -75° to -65° C. After stirring for 25 min. at -75° C. the solution is treated with 136g (0.576 mol) of ethyl 7-bromoheptanoate during 40 min. -75° to -65° C. After slow addition of 280 ml of TMF as rinse the mixture is stirred at -75° C. for 2.5 hr. and at ambient temperature for 18 hr. The reaction mixture is partitioned with water and ether. The ether phase is washed with brine, dried over sodium sulfate, filtered through Celite, and concentrated.

Workup

  1. temperatureis cooled to -75° C.
  2. stirringAfter stirring for 25 min. at -75° C. the solution
  3. additionAfter slow addition of 280 ml of TMF
  4. washas rinse the mixture
  5. stirringis stirred at -75° C. for 2.5 hr
  6. waitand at ambient temperature for 18 hr
  7. customThe reaction mixture is partitioned with water and ether
  8. washThe ether phase is washed with brine
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered through Celite
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-d13e41016c574999a01beb05ec7ae6c6
Source dataset
uspto-grants-1978_02
Patent number
US04076732

Reaction notes

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