Water → 1-Azolyl-4-phenyl-2-butanone, 6a

HRID 2198781ノート

反応式

HRID 2198781 の反応式
C(Cl)(=O)C(Cl)=O.[OH:7][CH:8]([CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:9][N:10]1[CH:14]=[CH:13][N:12]=[CH:11]1.C(N(CC)CC)C.O>C(Cl)Cl.CS(C)=O>[C:17]1([CH2:16][CH2:15][C:8](=[O:7])[CH2:9][N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

参加物

7

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 134573551-(2-Hydroxy-4-phenylbutyl)imidazole

生成物 1

HCID 128164661-Azolyl-4-phenyl-2-butanone, 6a

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒2 回HCID 6344Dichloromethane溶媒3 回

実験手順

Oxalyl chloride (2.0 ml) in methylene chloride (40 ml) was placed in a flask and cooled to -50° C. to -60° C. Dimethyl sulfoxide (3.0 ml) in 10 ml of methylene chloride was then added followed by 2.3 g of 1-(2-hydroxy-4-phenylbutyl)imidazole dissolved in 20 ml of methylene chloride containing 0.5 ml of dimethyl sulfoxide. The reaction mixture was stirred for 30 minutes at the initial temperature. Triethylamine (7 ml) was added to the reaction mixture which was then allowed to warm to room temperature. Water was added, the organic layer separated and the aqueous layer extracted with methylene chloride (2×50 ml). The organic layers were dried over MgSO4, the solvent removed and the residue recrystallized from ethyl acetate to give 1-(4-phenylbutan-2-on-1-yl)imidazole. The hydrochloride salt crystallized from methanol/ethyl acetate had a melting point of 172°-173° C.

後処理

  1. temperaturecooled to -50° C. to -60° C
  2. customthe organic layer separated
  3. extractionthe aqueous layer extracted with methylene chloride (2×50 ml)
  4. dry with materialThe organic layers were dried over MgSO4
  5. customthe solvent removed
  6. customthe residue recrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-4f6b8fba5fe94c9ea2fb2292f4d526b4
出典データセット
uspto-grants-1982_11
特許番号
US04359475

反応ノート

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