Hydrochloric Acid → HCID 22648854、化合物

HRID 393284ノート

反応式

HRID 393284 の反応式
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([CH3:12])[CH:6]=1)=O.CC[N:15]([CH2:18]C)CC.[C:20]1([C:26](Cl)([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Cl.C([NH2:43])=O>CN(C=O)C.CCOC(C)=O>[CH3:12][C:7]1[CH:6]=[C:5]([C:3]2[N:43]=[CH:18][N:15]([C:26]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:2]=2)[CH:10]=[CH:9][C:8]=1[OH:11]

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 713FormamideHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 112184492-Bromo-1-(4-hydroxy-3-methylphenyl)ethanone

生成物 1

HCID 22648854HCID 22648854、化合物収率 71%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
25 °C

実験手順

A solution of 2-bromo-1-(4-hydroxy-3-methylphenyl)ethanone (400 mg, 1.75 mmol) in formamide (10 mL) was stirred at 190° C. for 5 h. The excess formamide was distilled under reduced pressure. The residue was taken in EtOAc (50 mL) and the resulting solution was successively washed with pH 7.0 buffer solution (10 mL), water (10 mL) and brine (10 mL) then was dried (MgSO4), filtered and concentrated under reduced pressure. A solution of the residue, Et3N (0.88 g, 8.73 mmol) and triphenylmethyl chloride (584 mg, 2.10 mmol) in DMF (10 mL) was stirred at 60° C. for 3 h. The reaction mixture was cooled to 25° C., acidified with aqueous 1.0 N HCl solution and diluted with EtOAc (200 mL). The resulting mixture was successively washed with water (3×50 mL) and brine (50 mL), then dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (Hexane:EtOAc, 1:1) to yield the title compound (514 mg, 71% yield).

後処理

  1. distillationThe excess formamide was distilled under reduced pressure
  2. washthe resulting solution was successively washed with pH 7.0 buffer solution (10 mL), water (10 mL) and brine (10 mL)
  3. dry with materialthen was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. washThe resulting mixture was successively washed with water (3×50 mL) and brine (50 mL)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by flash chromatography (Hexane:EtOAc, 1:1)

出典と根拠

ORDレコード
ord-ffd4d76f870e4305ac6cc04a520d9816
出典データセット
uspto-grants-2004_10
特許番号
US06806265B2

反応ノート

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