Acetyl chloride → HCID 22917845, compound

HRID 1608884Notes

Reaction equation

HRID 1608884 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[Cl:5][C:6]1([Cl:25])[C@H:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C@@H:7]1[C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22](=[O:24])[CH3:23])=[CH:17][CH:16]=1>N1C=CC=CC=1>[Cl:5][C:6]1([Cl:25])[CH:8]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:7]1([C:15]1[CH:16]=[CH:17][C:18]([O:21][C:22](=[O:24])[CH3:23])=[CH:19][CH:20]=1)[C:6]1[CH:7]=[CH:15][C:1]([O:3][C:18](=[O:21])[CH3:17])=[CH:2][CH:8]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 67708224HCID 67708224, compound

Product 1

HCID 22917845HCID 22917845, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetylation of Compound 36 (0.6 g, 0.0016 mol) was performed with pyridine (0.8 mL) and acetyl chloride (0.8 mL) as described in the preparation of Compound 10. The crude product was chromatographed (silica gel; CH2Cl2 /acetone, 98:2) to provide 0.02 g colorless amorphous solid, mp 74°-75° C. The fractions eluted with CH2Cl2 /acetone (95:5) had both the acetate and the phenolic products, which were subjected to acetylation. Additional purification provided a total 0.1 g of Compound 37 (13.7%). 1H NMR (CDCl3) δ 2.26 (s, 6H, OCOCH3), 3.55 (s, 1H, ArCH), 6.96-7.66 (m, 13H, ArH).

Workup

  1. customThe crude product was chromatographed (silica gel; CH2Cl2 /acetone, 98:2)

Sources & evidence

ORD record
ord-f4de84ed7800440b9a36ef0babad1bdd
Source dataset
uspto-grants-1995_03
Patent number
US05397802

Reaction notes

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