2-Methylbenzenesulfonic acid → HCID 69522022, 화합물

HRID 460021

반응식

HRID 460021 반응식
[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

참가 물질

7

반응물 4

HCID 69252-Methylbenzenesulfonic acidHCID 2724682Lithium diisopropylamideHCID 27828994-Methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbaldehyde2회HCID 1296932556443-69-72회

생성물 1

HCID 69522022HCID 69522022, 화합물

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1cee6bc02cd2484b9ffb34dbfe215a32
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07196107B2

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