Potassium Carbonate → 1-{5'-[3,4-Bis(benzoyloxymethyl)benzyloxy]-2'methyl-2-propylbiphenyl-4-yl}-1-propanone

HRID 584292ノート

反応式

HRID 584292 の反応式
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:21])=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:17])[CH2:15][CH3:16])=[CH:10][C:9]=2[CH2:18][CH2:19][CH3:20])[CH:7]=1.[C:22]([O:30][CH2:31][C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][C:39]=1[CH2:40][O:41][C:42](=[O:49])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[CH2:35]Br)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[C:22]([O:30][CH2:31][C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][C:39]=1[CH2:40][O:41][C:42](=[O:49])[C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)[CH2:35][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:21])=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:17])[CH2:15][CH3:16])=[CH:10][C:9]=2[CH2:18][CH2:19][CH3:20])[CH:7]=1)(=[O:29])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 223455921-(5'-Hydroxy-2'-methyl-2-propylbiphenyl-4-yl)-1-propanoneHCID 223456183,4-Bis(benzoyloxymethyl)benzyl bromide

生成物 1

HCID 223456301-{5'-[3,4-Bis(benzoyloxymethyl)benzyloxy]-2'methyl-2-propylbiphenyl-4-yl}-1-propanone収率 56%

試薬・触媒・溶媒 1

HCID 6569Methyl Ethyl Ketone溶媒

実験手順

1.5 g (5.4 mmol) of 1-(5′-hydroxy-2′-methyl-2-propylbiphenyl-4-yl)-1-propanone, 2.5 g (5.7 mmol) of (3,4-bis(benzoyloxymethyl)benzyl bromide and 750 mg (5.4 mmol) of potassium carbonate are placed in 50 ml of methyl ethyl ketone in a round-bottomed flask and under a stream of nitrogen. The mixture is refluxed overnight and, after cooling, it is filtered through Celite. The filtrate is extracted with water and ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and then evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a mixture of heptane and ethyl acetate (85/15) to give 1.93 g (56%) of the expected product in the form of a dark yellow oil.

後処理

  1. temperatureThe mixture is refluxed overnight
  2. temperatureafter cooling
  3. filtrationit is filtered through Celite
  4. extractionThe filtrate is extracted with water and ethyl acetate
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue obtained
  9. customis purified by chromatography on a column of silica
  10. washeluted with a mixture of heptane and ethyl acetate (85/15)

出典と根拠

ORDレコード
ord-9a10ba9d8ca14987ade8df95d7112f3f
出典データセット
uspto-grants-2005_08
特許番号
US06924400B2

反応ノート

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