Hydrochloric Acid → HCID 178497922, compound

HRID 1763166Notes

Reaction equation

HRID 1763166 reaction equation
[O:1]=[C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([CH:12]([CH3:14])[CH3:13])OC(C(F)(F)F)=[C:3]1[C:19]([O:21][CH3:22])=[O:20].[C:23]([C:27]#[N:28])([Cl:26])([Cl:25])[F:24].C1CCN2C(=NCCC2)CC1.Cl>COCCOC>[Cl:25][C:23]([Cl:26])([F:24])[C:27]1[C:3]([C:19]([O:21][CH3:22])=[O:20])=[C:2]([OH:1])[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([CH:12]([CH3:14])[CH3:13])[N:28]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 520730Dichloro(fluoro)acetonitrileHCID 14373431HCID 14373431, compound

Product 1

HCID 178497922HCID 178497922, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 17.80 g (0.073 mol) of dimethyl 2-(isobutyryl)-3-oxo-1,5-pentendioate (Step B of Example 208) in 300 mL of DME at -78° C. was added 18 g (0.4 mol) of CFCl2CN followed by 11.1 g (11 ml, 0.073 mol) of DBU. The reaction was warmed up to 25° C., poured into 3.7% HCl, and extracted twice with EtOAc. The EtOAc extract was washed again with 3.7% HCl, saturated NaCl and dried (MgSO4). The solvent was removed in vacuo to give 25.88 g of a dark brown solid. The crude was purified by HPLC using 2% HOAc/16% EtOAc/82% cyclohexane as eluting solvent, affording 21 g (81%) of product as a beige solid. For elemental analysis a portion of this solid was washed with hexane affording the product as a white solid: mp 75°-76° C.

Workup

  1. extractionextracted twice with EtOAc
  2. extractionThe EtOAc extract
  3. washwas washed again with 3.7% HCl, saturated NaCl
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-701578ccc1574c328c6f4f3f768e3be1
Source dataset
uspto-grants-1989_05
Patent number
US04835279

Reaction notes

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