Cesium carbonate → Ethyl 7-(3-(3-trifluoromethyl-7-propyl-6-benz-[4,5]-isoxazoloxy)propoxy)-2-ethylchromane-2-carboxylate

HRID 51075ノート

反応式

HRID 51075 の反応式
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([CH2:10][CH2:11][C:12]([CH2:21][CH3:22])([C:16]([O:18][CH2:19][CH3:20])=[O:17])[O:13]2)=[CH:8][CH:7]=1.[F:23][C:24]([F:39])([F:38])[C:25]1[C:29]2[CH:30]=[CH:31][C:32]([OH:37])=[C:33]([CH2:34][CH2:35][CH3:36])[C:28]=2[O:27][N:26]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[F:39][C:24]([F:23])([F:38])[C:25]1[C:29]2[CH:30]=[CH:31][C:32]([O:37][CH2:2][CH2:3][CH2:4][O:5][C:6]3[CH:15]=[C:14]4[C:9]([CH2:10][CH2:11][C:12]([CH2:21][CH3:22])([C:16]([O:18][CH2:19][CH3:20])=[O:17])[O:13]4)=[CH:8][CH:7]=3)=[C:33]([CH2:34][CH2:35][CH3:36])[C:28]=2[O:27][N:26]=1

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 22737362Ethyl 7-(3-bromopropoxy)-2-ethylchromane-2-carboxylateHCID 1358008127-Propyl-3-(trifluoromethyl)benzo[d]isoxazol-6-ol

生成物 1

HCID 69898123Ethyl 7-(3-(3-trifluoromethyl-7-propyl-6-benz-[4,5]-isoxazoloxy)propoxy)-2-ethylchromane-2-carboxylate収率 85%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

To a 2 ml DMF solution of ethyl 7-(3-bromopropoxy)-2-ethylchromane-2-carboxylate (40 mg, 0.108 mmol) and 3-trifluoromethyl-7-propyl-6-hydroxybenzisoxazole (U.S. Pat. No. 6,090,836) (29 mg, 0.118 mmol) was added cesium carbonate (39 mg, 0.12 mmol). The resulting suspension was heated to 70° C. for 5 hr. The solvent was removed under reduced pressure. The residue was diluted with AcOEt and water. The organic layer was separated, and the aqueous layer was extracted twice with AcOEt. The combined organic layers were dried over anhydrous Na2SO4, filtered, concentrated, and chromatographed on silica gel. Elution with 20% AcOEt/hexanes gave the title compound as a pale yellow oil 49 mg (85%).

後処理

  1. customThe solvent was removed under reduced pressure
  2. additionThe residue was diluted with AcOEt and water
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted twice with AcOEt
  5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed on silica gel
  9. washElution with 20% AcOEt/hexanes

出典と根拠

ORDレコード
ord-0f682bf914234a3cb79023e25a704622
出典データセット
uspto-grants-2004_03
特許番号
US06713508B2

反応ノート

読み込み中…