(+-)-2-Butanol → HCID 20089833, compound

HRID 1196132Notes

Reaction equation

HRID 1196132 reaction equation
F[C:2]1[CH:19]=[CH:18][C:17]2[C:16](=[O:20])[C:15]3[C:6](=[CH:7][C:8]4[C:13]([CH:14]=3)=[CH:12][CH:11]=[CH:10][CH:9]=4)[C:5](=[O:21])[C:4]=2[CH:3]=1.[C:22]([O-:25])([O-])=O.[Cs+].[Cs+].[CH3:28][CH2:29][CH:30](O)C>CN(C=O)C>[CH2:22]([O:25][C:2]1[CH:19]=[CH:18][C:17]2[C:16](=[O:20])[C:15]3[C:6](=[CH:7][C:8]4[C:13]([CH:14]=3)=[CH:12][CH:11]=[CH:10][CH:9]=4)[C:5](=[O:21])[C:4]=2[CH:3]=1)[CH2:30][CH:29]=[CH2:28]

Participants

5

Reactant 3

HCID 6568(+-)-2-ButanolHCID 10796Cesium carbonateHCID 200898282-Fluorotetracene-5,12-dione

Product 1

HCID 20089833HCID 20089833, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

10 g (0.036 mol) of 2-fluoro-5,12-naphthacenequinone, 26 g (0.028 mol) of Cs2CO3 and 10.41 g (0.14 mol) of 3-butanol are introduced into 200 ml of DMF under nitrogen. The reaction mixture is heated to 125° C. and stirred for 41/2 h. After precipitation in 4000 ml of water containing hydrochloric acid, the product is filtered off (crude yield 94%). Chromatography on silica gel (CH2Cl2) gives 63% pure product; melting point 149° C. The procedure in Examples 25-27 is analogous (see Table 2).

Workup

  1. customAfter precipitation in 4000 ml of water
  2. additioncontaining hydrochloric acid
  3. filtrationthe product is filtered off (crude yield 94%)

Sources & evidence

ORD record
ord-313ca6cf456943e18dd860f8d583f123
Source dataset
uspto-grants-1992_05
Patent number
US05112977

Reaction notes

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