Acetyl chloride → HCID 20078945, compound

HRID 1653962Notes

Reaction equation

HRID 1653962 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH2:9][C:10]([O:12][CH:13]2[CH:17]([OH:18])[CH2:16][O:15][CH2:14]2)=[O:11])=[CH:6][C:5]([N:19]2[C:23](=[O:24])[C:22]3[CH2:25][CH2:26][CH2:27][CH2:28][C:21]=3[C:20]2=[O:29])=[C:4]([F:30])[CH:3]=1.C(N(CC)CC)C.[C:38](Cl)(=[O:40])[CH3:39]>C1C=CC=CC=1>[C:38]([O:18][CH:17]1[CH2:16][O:15][CH2:14][CH:13]1[O:12][C:10]([CH2:9][O:8][C:7]1[C:2]([Cl:1])=[CH:3][C:4]([F:30])=[C:5]([N:19]2[C:20](=[O:29])[C:21]3[CH2:28][CH2:27][CH2:26][CH2:25][C:22]=3[C:23]2=[O:24])[CH:6]=1)=[O:11])(=[O:40])[CH3:39]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 15789768HCID 15789768, compound

Product 1

HCID 20078945HCID 20078945, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

In 15 ml of benzene were dissolved 0.66 g of N-(4-chloro-2-fluoro-5-(4-hydroxytetrahydrofuran-3-yloxycarbonylmethoxy)phenyl)-3,4,5,6tetrahydrophthalimide and 0.20 g of triethylamine, followed by dropwise addition of a solution of 0.14 g of acetyl chloride in benzene. After stirring at room temperature for 4 hours, the reaction mixture was washed with water and subsequently with aqueous saturated sodium chloride solution, and 'dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was purified by chromatography on a silica gel column (eluted with ethyl acetate/hexane=2/3), to obtain 0.55 g of a compound described in Table 1 (No.3) (76%).

Workup

  1. washthe reaction mixture was washed with water and subsequently with aqueous saturated sodium chloride solution
  2. dry with material'dried over anhydrous magnesium sulfate
  3. distillationAfter distilling off the solvent
  4. customthe residue was purified by chromatography on a silica gel column (eluted with ethyl acetate/hexane=2/3)

Sources & evidence

ORD record
ord-a9fedd2b36ca4955888418fced518c65
Source dataset
uspto-grants-1995_04
Patent number
US05405828

Reaction notes

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