Tert-butyl 2-[4-(bromomethyl)phenoxy]-2,2-difluoroacetate → Methyl 4-[1-{4-[2-(tert-butoxy)-1,1-difluoro-2-oxoethoxy]benzyl}-2-(4-fluorophenyl)-2-oxoethyl]benzoate

HRID 1371018ノート

反応式

HRID 1371018 の反応式
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[O:12])=[CH:6][CH:5]=1.CC(C)([O-])C.[K+].Br[CH2:28][C:29]1[CH:45]=[CH:44][C:32]([O:33][C:34]([F:43])([F:42])[C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])=[CH:31][CH:30]=1>C1COCC1>[C:38]([O:37][C:35](=[O:36])[C:34]([F:43])([F:42])[O:33][C:32]1[CH:31]=[CH:30][C:29]([CH2:28][CH:10]([C:7]2[CH:6]=[CH:5][C:4]([C:3]([O:2][CH3:1])=[O:20])=[CH:9][CH:8]=2)[C:11]([C:13]2[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=2)=[O:12])=[CH:45][CH:44]=1)([CH3:41])([CH3:39])[CH3:40]

参加物

5

反応物 3

HCID 15391315Tert-butyl 2-[4-(bromomethyl)phenoxy]-2,2-difluoroacetateHCID 18510220Methyl 4-[2-(4-fluorophenyl)-2-oxoethyl]benzoateHCID 23665647Potassium tert-butoxide

生成物 1

HCID 18510241Methyl 4-[1-{4-[2-(tert-butoxy)-1,1-difluoro-2-oxoethoxy]benzyl}-2-(4-fluorophenyl)-2-oxoethyl]benzoate収率 60.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of methyl-4-[2-(4-fluorophenyl)-2-oxoethyl]benzoate (0.150 g, 0.551 mmol) (Example 1, Step 2) in degassed THF at −20° C. was added potassium tert-butoxide (0.606 ml), followed by a solution of tert-butyl 2-[4-(bromomethyl)phenoxy]-2,2-difluoroacetate (H. Fretz, Tetrahedron 54, 4849, 1998) (0.203 g, 0.604 mmol) in THF (0.5 ml). The reaction was allowed to warm slowly to room temperature, and was then quenched with saturated ammonium acetate solution and extracted with ethyl acetate. The organic phase was dried over sodium sulfate, filtered and evaporated to dryness. The residue was purified by flash chromatography using toluene/ethyl acetate 5% giving 0.176 g of the title compound.

後処理

  1. customwas then quenched with saturated ammonium acetate solution
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-88b879f0a0234b94b02516e1f9d2a99b
出典データセット
uspto-grants-2003_06
特許番号
US06583126B2

反応ノート

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