Benzaldehyde → HCID 70351301, compound

HRID 1032366Notes

Reaction equation

HRID 1032366 reaction equation
C([Li])CCC.CC(C)=O.C(=O)=O.[Cl:13][C:14]1[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=1[CH:21]1[C:26]([C:27]([O:29][CH3:30])=[O:28])=[C:25]([CH3:31])[NH:24][C:23]([CH2:32][O:33][CH2:34][C:35]#[CH:36])=[C:22]1[C:37]([O:39][CH2:40][CH3:41])=[O:38].[CH:42](=[O:49])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>CCCCCC.O1CCCC1>[Cl:13][C:14]1[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=1[CH:21]1[C:26]([C:27]([O:29][CH3:30])=[O:28])=[C:25]([CH3:31])[NH:24][C:23]([CH2:32][O:33][CH2:34][C:35]#[C:36][CH:42]([OH:49])[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[C:22]1[C:37]([O:39][CH2:40][CH3:41])=[O:38]

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 14547436HCID 14547436, compoundHCID 18522661Acetone cardiceHCID 178418339Butyllithium

Product 1

HCID 70351301HCID 70351301, compoundYield 21.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A 1.6M solution of n-butyllithium in hexane (3.4 ml) was added dropwise over 15 minutes to a stirred, cooled (acetone/cardice bath) solution of 1-{[4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyrid-2-yl]methoxy}prop-2-yne (1.10 g) in tetrahydrofuran (25 ml) and the mixture stirred at -70° for 2 hours. The mixture was then allowed to warm up to between -35° and -40°, stirred at that temperature for 2 hours, treated dropwise with a solution of benzaldehyde (0.16 g) in tetrahydrofuran (5 ml) over 5 minutes and then stirred at between -10° and -15° for one hour and at room temperature for 14 hours. The reaction mixture was partitioned between ethyl acetate and water and the organic layer washed with water, dried over Na2SO4 and evaporated. The residue was triturated with diethyl ether and the resulting solid collected, washed with diethyl ether and dried to give the title compound (0.18 g), m.p. 160°-164°.

Workup

  1. temperatureto warm up to between -35° and -40°
  2. stirringstirred at that temperature for 2 hours
  3. stirringstirred at between -10° and -15° for one hour and at room temperature for 14 hours
  4. customThe reaction mixture was partitioned between ethyl acetate and water
  5. washthe organic layer washed with water
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customThe residue was triturated with diethyl ether
  9. customthe resulting solid collected
  10. washwashed with diethyl ether
  11. customdried

Sources & evidence

ORD record
ord-711204afd99445fbba492ac11dfcbe78
Source dataset
uspto-grants-1990_09
Patent number
US04957930

Reaction notes

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