2-Methylbenzenesulfonic acid → HCID 69522022、化合物

HRID 460021

反応式

HRID 460021 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][C:10]=1[CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N-]C(C)C)(C)C.[Li+].[CH3:27][C:28]1[N:29]=[C:30]([C:35]2[CH:40]=[CH:39][C:38]([C:41]([F:44])([F:43])[F:42])=[CH:37][CH:36]=2)[S:31][C:32]=1[CH:33]=O.C1(C)C(S(O)(=O)=O)=CC=CC=1>O1CCCC1.C(O)(=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH:16]=[CH:33][C:32]2[S:31][C:30]([C:35]3[CH:36]=[CH:37][C:38]([C:41]([F:44])([F:42])[F:43])=[CH:39][CH:40]=3)=[N:29][C:28]=2[CH3:27])=[CH:11][C:10]=1[CH3:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 69252-Methylbenzenesulfonic acidHCID 2724682Lithium diisopropylamideHCID 27828994-Methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbaldehyde2 回HCID 1296932556443-69-72 回

生成物 1

HCID 69522022HCID 69522022、化合物

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
0 °C

実験手順

A mixture of 1-[4-(benzyloxy)-3-methylphenyl]ethanone (intermediate 8, 1.15 g) in dry tetrahydrofuran (15 ml) at −78° C. was treated dropwise with lithium diisopropylamide (2.6 ml of 2M solution in heptane/tetrahydrofuran/ethylbenzene) under nitrogen. The reaction mixture was warmed to 0° C. for 30 minutes. The mixture was cooled to −78° C. and 4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbaldehyde (intermediate 2, 1.08 g) in dry tetrahydrofuran (15 ml) was added drop-wise at −78° C. and the reaction mixture stirred at 21° C. for 2 hours. Acetic acid (4 ml) in dry tetrahydrofuran (4 ml) was added followed by toluenesulphonic acid (0.1 g) and the reaction mixture was heated at 50° C. for 1 hour and then concentrated. The residue was partitioned between saturated bicarbonate solution and ethyl acetate; the aqueous layer separated and extracted thrice more with ethyl acetate. The organic solutions were combined and were dried with brine and over magnesium sulfate and concentrated. The product isolated after evaporation of the solvent was further purified by flash chromatography using cyclohexane:ethyl acetate (6:1) as eluent to give the title compound as a yellow solid.

後処理

  1. temperatureThe mixture was cooled to −78° C.
  2. temperaturethe reaction mixture was heated at 50° C. for 1 hour
  3. concentrationconcentrated
  4. customThe residue was partitioned between saturated bicarbonate solution and ethyl acetate
  5. customthe aqueous layer separated
  6. extractionextracted thrice more with ethyl acetate
  7. dry with materialwere dried with brine and over magnesium sulfate
  8. concentrationconcentrated
  9. customThe product isolated
  10. customafter evaporation of the solvent
  11. customwas further purified by flash chromatography

出典と根拠

ORDレコード
ord-1cee6bc02cd2484b9ffb34dbfe215a32
出典データセット
uspto-grants-2007_03
特許番号
US07196107B2

関連ノート

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