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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
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HRID 1452691 반응식
[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
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참가 물질

7

반응물 4

HCID 962WaterHCID 7276Styrene OxideHCID 10796Cesium carbonateHCID 86604220HCID 86604220, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 3283
Diethyl Ether
용매
HCID 312751,4-Dioxane용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-7f676de20d8b4b9e8e054c4f4976a154
출처 데이터셋
uspto-grants-2009_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07473705B2

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