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Potassium Hydroxide → (5R)-3-(5-bromo-2-pyridyloxy)-4-(4-methylsulfonylphenyl)-5-methyl-5-(2,2,2-trifluoroethyl)-5H-furan-2-one

HRID 1106611
ノート
印刷プレビュー

反応式

HRID 1106611 の反応式
[CH3:1][C:2]1([CH2:19][C:20]([F:23])([F:22])[F:21])[C@@:7]2([C:8]3[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=3)[CH:5]([O:6]2)[C:4](=[O:18])[O:3]1.[K].[Br:25][C:26]1[CH:27]=[CH:28][C:29](O)=[N:30][CH:31]=1.[OH-].[K+]>CN(C)C=O.C(O)(C)C>[Br:25][C:26]1[CH:27]=[CH:28][C:29]([O:6][C:5]2[C:4](=[O:18])[O:3][C@:2]([CH3:1])([CH2:19][C:20]([F:23])([F:22])[F:21])[C:7]=2[C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)=[N:30][CH:31]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 14797Potassium HydroxideHCID 5462222PotassiumHCID 21968267(5R)-4-methyl-4-(2,2,2-trifluoroethyl)-5-(4-methylsulfonylphenyl)-3,6-dioxabicyclo[3,1,0]hexan-2-oneHCID 178515818HCID 178515818、化合物2 回

生成物 1

HCID 18397164(5R)-3-(5-bromo-2-pyridyloxy)-4-(4-methylsulfonylphenyl)-5-methyl-5-(2,2,2-trifluoroethyl)-5H-furan-2-one

試薬・触媒・溶媒 2

HCID 3776Isopropanol溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a 0° C. mixture of the epoxide (0.930 g) from step 1 in dimethylformamide (3 mL) and isopropanol (12 mL) was added the potassium salt of 5-bromo-2-hydroxypyridine, prepared from 5-bromo-2-hydroxypyridine and one equivalent of 8N KOH followed by evaporation to dryness with toluene and high vacuum drying, (0.742 g, 3.5 mmol) and the mixture was warmed up slowly to reflux for 16 hrs. It was then cooled to room temperature and poured on icy dilute ammonium chloride and ethyl acetate; the organic layer was separated and the aquous further extracted ounce with ethyl acetate. The combined organic layers were washed with brine, dried with MgSO4 and the solvents were removed in vacuo to yield after purification on silica gel (10% acetone/toluene) the title compound (0.380 g).

後処理

  1. customfollowed by evaporation to dryness with toluene and high vacuum
  2. customdrying
  3. temperature(0.742 g, 3.5 mmol) and the mixture was warmed up slowly
  4. temperatureto reflux for 16 hrs
  5. additionpoured on icy dilute ammonium chloride and ethyl acetate
  6. customthe organic layer was separated
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried with MgSO4
  9. customthe solvents were removed in vacuo
  10. customto yield
  11. customafter purification on silica gel (10% acetone/toluene) the title compound (0.380 g)

出典と根拠

ORDレコード
ord-eaceefa695304e56b4700f02c1cbe990
出典データセット
uspto-grants-2000_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06057319

反応ノート

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