Hydrochloric Acid → HCID 53915561, compound

HRID 330684Notes

Reaction equation

HRID 330684 reaction equation
[C:1]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].C([Li])CCC.[F:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([C:38]2[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=2)=[C:27]([C:32]2[N:36]([CH3:37])[N:35]=[N:34][N:33]=2)[CH:28]=[CH:29][CH:30]=[O:31])=[CH:22][CH:21]=1.Cl>O1CCCC1.CCCCCC>[F:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]([C:38]2[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=2)=[C:27]([C:32]2[N:36]([CH3:37])[N:35]=[N:34][N:33]=2)[CH:28]=[CH:29][CH:30]([OH:31])[CH2:5][C:3](=[O:4])[CH2:2][C:1]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])=[CH:24][CH:25]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 15538Tert-butyl acetoacetateHCID 24758Sodium hydrideHCID 53904180HCID 53904180, compoundHCID 178418339Butyllithium

Product 1

HCID 53915561HCID 53915561, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent2×

Procedure

A solution of 144 g (0.91 mol) of t-butyl acetoacetate in 400 mL of tetrahydrofuran was added dropwise over 1.5 hours to a mixture of 44.0 g (1.10 mol) of sodium hydride (60% in mineral oil) in 100 mL of hexane and 500 mL of tetrahydrofuran under nitrogen at 0° C. After the addition, this mixture was stirred for 2.3 hours. A solution 2.5M n-butyllithium in hexane (360 mL, 0.91 mol) was added dropwise over 1 hour. After stirring at 0° C. for 1 hour, 200 g (0.57 mol) of the aldehyde prepared in Step A was added all at once and the temperature rose to 20° C. After stirring for 1 hour in an ice-water bath, 1200 mL of 10% aqueous hydrochloric acid was added over 1 hour. The organic layer was washed with 2×300 mL of water, 300 mL of saturated sodium chloride solution, dried with anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to give the title compound which was used without further purification.

Workup

  1. additionAfter the addition
  2. stirringAfter stirring at 0° C. for 1 hour
  3. customrose to 20° C
  4. stirringAfter stirring for 1 hour in an ice-water bath
  5. washThe organic layer was washed with 2×300 mL of water, 300 mL of saturated sodium chloride solution
  6. dry with materialdried with anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-0137d909dc874b2288f67ff0120d8547
Source dataset
uspto-grants-1990_01
Patent number
US04897490

Reaction notes

Loading…