Acetic Acid → HCID 53700889, compound

HRID 2108248Notes

Reaction equation

HRID 2108248 reaction equation
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[CH2:9]([Li])CCC.[H-].[Na+].[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:27]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)=[C:26]([CH:35]=[CH:36][CH:37]=[O:38])[N:25]([CH:39]([CH3:41])[CH3:40])[C:24]=2[CH:42]=[CH:43][CH:44]=[O:45])=[CH:19][CH:18]=1.[C:46]([OH:49])(=[O:48])[CH3:47].[O:50]1CC[CH2:52][CH2:51]1>CCCCCC>[F:34][C:31]1[CH:32]=[CH:33][C:28]([C:27]2[C:23]([C:20]3[CH:21]=[CH:22][C:17]([F:16])=[CH:18][CH:19]=3)=[C:24]([CH:42]=[CH:43][CH:44]([OH:45])[CH2:5][C:3](=[O:4])[CH2:2][C:1]([O:7][CH3:8])=[O:6])[N:25]([CH:39]([CH3:40])[CH3:41])[C:26]=2[CH:35]=[CH:36][CH:37]([OH:38])[CH2:52][C:51](=[O:50])[CH2:47][C:46]([O:49][CH3:9])=[O:48])=[CH:29][CH:30]=1

Participants

8

Reactant 6

HCID 176Acetic AcidHCID 7757Methyl acetoacetateHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 53853635HCID 53853635, compoundHCID 178418339Butyllithium

Product 1

HCID 53700889HCID 53700889, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

0.35 ml (3.25 mmol) of methyl acetoacetate and then at about 0° C. 2.72 ml (4.43 mmol) of a 15% strength solution of butyllithium in hexane are added slowly under argon to a suspension of 107 mg (3.56 mmol) of 80% strength sodium hydride in 10 ml of anhydrous tetrahydrofuran at -5° C. After stirring for 15 minutes at 0° C., a solution of 0.6 g (1.48 ml) of the compound from Example 6 in 5 ml of tetrahydrofuan is added dropwise and the mixture is stirred for a further 15 minutes at the same temperature. Finally, 0.58 g (9.67 mmol) of acetic acid is cautiously added dropwise and then 50 ml of water, the mixture is extracted three times using ethyl acetate and the organic phase is dried over sodium sulphate and sodium carbonate. After stripping off the solvent, 0.94 g of reddish foam remain of Rf value: 0.2 using toluene/ethyl acetate (1:1). The crude product is processed further.

Workup

  1. customat about 0° C
  2. stirringthe mixture is stirred for a further 15 minutes at the same temperature
  3. extraction50 ml of water, the mixture is extracted three times
  4. dry with materialthe organic phase is dried over sodium sulphate and sodium carbonate

Sources & evidence

ORD record
ord-e53be9e2114f4d23924ca6b6d5d729ed
Source dataset
uspto-grants-1990_06
Patent number
US04937255

Reaction notes

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