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Water → Rac 1-phenyl-2-{3-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-ethanol

HRID 1452691
ノート
印刷プレビュー

反応式

HRID 1452691 の反応式
[F:1][C:2]([F:26])([F:25])[C:3]([C:18]1[CH:19]=[C:20]([OH:24])[CH:21]=[CH:22][CH:23]=1)([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)[C:4]([F:7])([F:6])[F:5].[C:27]1([CH:33]2[CH2:35][O:34]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C([O-])([O-])=O.[Cs+].[Cs+].O>O1CCOCC1.CCOCC>[C:27]1([CH:33]([OH:34])[CH2:35][O:24][C:20]2[CH:21]=[CH:22][CH:23]=[C:18]([C:3]([O:8][CH2:9][C:10]3[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=3)([C:4]([F:6])([F:5])[F:7])[C:2]([F:25])([F:26])[F:1])[CH:19]=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=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 962WaterHCID 7276Styrene OxideHCID 10796Cesium carbonateHCID 86604220HCID 86604220、化合物

生成物 1

HCID 87605889Rac 1-phenyl-2-{3-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-ethanol収率 62.3%

試薬・触媒・溶媒 2

HCID 3283
Diethyl Ether
溶媒
HCID 312751,4-Dioxane溶媒

実験手順

To 1 g (2.6 mmol) of 3-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenol (example 5) in 8 mL of dioxane were added 1.0 mL (8.8 mmol) of 2-phenyl-oxirane. The reaction was split in 2 portions. To each of those was added 4.28 g (13.1 mmol) of Cs2CO3 and each reaction mixture was treated for 30 min at 130° C. in the microwave. The mixtures were combined and water and ether were added. The aqueous phase was extracted with ether and the combined organic phases were washed with brine and dried (Na2SO4). After evaporation of the solvent the crude products were separated by column chromatography to give 810 mg (62%) of rac 1-phenyl-2-{3-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-ethanol as light yellow oil, MS: 500 (M)+, and 250 mg (19%) of rac 2-phenyl-2-{3-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-ethanol as light yellow oil, MS: 500 (M)+.

後処理

  1. customThe reaction was split in 2 portions
  2. additioneach reaction mixture was treated for 30 min at 130° C. in the microwave
  3. extractionThe aqueous phase was extracted with ether
  4. washthe combined organic phases were washed with brine
  5. dry with materialdried (Na2SO4)
  6. customAfter evaporation of the solvent the crude products
  7. customwere separated by column chromatography

出典と根拠

ORDレコード
ord-7f676de20d8b4b9e8e054c4f4976a154
出典データセット
uspto-grants-2009_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07473705B2

反応ノート

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