Pyridine → HCID 22117153, compound

HRID 1275541Notes

Reaction equation

HRID 1275541 reaction equation
[OH:1][C:2]1[C:3](=[O:26])[C:4]2[C:9]([C:10](=[O:25])[C:11]=1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])=[CH:8][CH:7]=[CH:6][CH:5]=2.N1C=CC=CC=1.[C:33](Cl)(=[O:36])[CH2:34][CH3:35]>ClCCl>[C:33]([O:1][C:2]1[C:3](=[O:26])[C:4]2[C:9]([C:10](=[O:25])[C:11]=1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][Si:21]([CH3:22])([CH3:23])[CH3:24])=[CH:8][CH:7]=[CH:6][CH:5]=2)(=[O:36])[CH2:34][CH3:35]

Participants

5

Reactant 3

HCID 1049PyridineHCID 62324Propionyl chlorideHCID 178504197HCID 178504197, compound

Product 1

HCID 22117153HCID 22117153, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 2-hydroxy-3-(9-trimethylsilylnonyl)-1,4-naphthoquinone, Example 12, (100 mg, 0.27 mmol) in dry dichloromethane (10 ml) at room temperature was added pyridine (0.5 ml) and, after 3 minutes, propanoyl chloride (62 mg, 0.67 mmol). The reaction was stirred for 2 h before diluting with dichloromethane (50 ml), washing with water (2×30 ml), dilute hydrocholic acid (30 ml), saturated sodium chloride solution (30 ml) and dried (MgSO4). Filtration and evaporation of the solvent under reduced pressure and chromatography, eluent hexane/ether, gave 2-propanoyloxy-3-(9-trimethylsilylnonyl)-1,4-naphthoquinone (112 mg). m. pt. 41-43° C. NMR peaks at: 184.6, 178.2, 151.2, 139.8, 134.0, 133.7, 132.1, 130.9, 126.7, 126.5, 33.6, 29.7, 29.4, 29.4, 29.3, 29.3, 28.5, 24.3, 23.9, 16.7, -1.6; 171.6, 27.3, 9.1 (COCH2CH3).

Workup

  1. washwashing with water (2×30 ml)
  2. additiondilute hydrocholic acid (30 ml), saturated sodium chloride solution (30 ml)
  3. dry with materialdried (MgSO4)
  4. filtrationFiltration and evaporation of the solvent under reduced pressure and chromatography, eluent hexane/ether

Sources & evidence

ORD record
ord-31336939a1dc4131948fc6901c242dd9
Source dataset
uspto-grants-2000_12
Patent number
US06162799

Reaction notes

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