Pivaloyl chloride → HCID 22647800, compound

HRID 1018739Notes

Reaction equation

HRID 1018739 reaction equation
[OH:1][C:2]1[C:3](=[O:13])[C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[C:14](Cl)(=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16]>C1C=CC=CC=1.[Ag]>[C:15]([C:14]([O:12][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](=[O:13])[C:2](=[O:1])[CH:11]=1)=[O:19])([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 2

HCID 62493Pivaloyl chlorideHCID 178516607HCID 178516607, compound

Product 1

HCID 22647800HCID 22647800, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 23954SilverCatalystHCID 241BenzeneSolvent

Procedure

A mixture of the silver salt of 2-hydroxy-1,4-naphthoquinone (842 mg, 3 mmol), and pivaloyl chloride (434 mg, 3.6 mmol) in benzene (5 mL) was stirred for 8 h at room temperature. The reaction mixture was filtered through Celite, the precipitate washed with EtOAc, and the combined organic solutions were concentrated in vacuo and purified by flash chromatography (EtOAc/hexane 1:10, 1:5). The product was recrystallized from hexane to afford a yellow solid (190 mg, 25%); mp 125-126° C.; 1H NMR (CDCl3) 8.15(dd, J=7.7, 1.1 Hz, 1H), 7.71(dt, J=7.7, 1.5 Hz, 1H), 7.59 (dt, J=7.5, 1.2 Hz, 1H), 7.57 (dd, J=7.6, 1.1 Hz, 1H), 6.48 (s, 1H), 1.44 (s, 9H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. washthe precipitate washed with EtOAc
  3. concentrationthe combined organic solutions were concentrated in vacuo
  4. custompurified by flash chromatography (EtOAc/hexane 1:10, 1:5)
  5. customThe product was recrystallized from hexane

Sources & evidence

ORD record
ord-05c0fc7fae7d444d806096b37de7f461
Source dataset
uspto-grants-2002_11
Patent number
US06482943B1

Reaction notes

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