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Ethylene Glycol → 1,4-Dioxaspiro[4.5]decane, 8-[4-(3,4-difluorophenyl)-3-cyclohexen-1-yl]-

HRID 2081521
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인쇄 미리보기

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HRID 2081521 반응식
[F:1][C:2]1[CH:3]=[C:4]([C:9]2(O)[CH2:14][CH2:13][CH:12]([CH:15]3[CH2:24][CH2:23][C:18]4([O:22][CH2:21][CH2:20][O:19]4)[CH2:17][CH2:16]3)[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8].C(O)CO.C[Si](O[Si](C)(C)C)(C)C.[O-2].[Al+3].[O-2].[O-2].[Al+3]>C(Cl)CCl>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH2:14][CH2:13][CH:12]([CH:15]3[CH2:24][CH2:23][C:18]4([O:19][CH2:20][CH2:21][O:22]4)[CH2:17][CH2:16]3)[CH2:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[F:8]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 174Ethylene GlycolHCID 24764HexamethyldisiloxaneHCID 9989226AluminaHCID 190011474-[4-Hydroxy-4-(3,4-difluorophenyl)cyclohexyl]cyclohexanone ethyleneacetal

생성물 1

HCID 115590611,4-Dioxaspiro[4.5]decane, 8-[4-(3,4-difluorophenyl)-3-cyclohexen-1-yl]-수율 66.2%

시약·촉매·용매 1

HCID 11
1,2-Dichloroethane
용매

실험 절차

A mixture of 7.8 g of crude 1-(3,4-difluorophenyl)-4-(1,4-dioxa-8-spiro[4.5]decyl) cyclohexanol, 1.05 ml of ethylene glycol, 1.05 g of Amberlyst® 15 (strongly acid ion exchange resin, Fluka AG) and 80 ml of ethylene chloride was refluxed through neutral aluminum oxide for 3 hours. Subsequently, the mixture was cooled to room temperature and washed twice with water. The aqueous phases were extracted twice with methylene chloride. The organic phases where dried over sodium sulfate, filtered and concentrated. Chromatographic purification of the residue on silica gel with hexane/ethyl acetate (vol. 96:4) gave 4,9 g of 8-[4-(3,4-difluorophenyl)-3-cyclohexenyl]-1,4-dioxaspiro [4.5]decane as colorless crystals.

후처리

  1. washwashed twice with water
  2. extractionThe aqueous phases were extracted twice with methylene chloride
  3. dry with materialThe organic phases where dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customChromatographic purification of the residue on silica gel with hexane/ethyl acetate (vol. 96:4)

출처 및 근거

ORD 기록
ord-5f710469012a4e4f8fa2477df165a849
출처 데이터셋
uspto-grants-1993_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05185098

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