Ammonium Chloride → 4-(1,4-Dioxaspiro[4.5]decan-8-yl)-1-(4-butoxy-2,3-difluorophenyl)-cyclohexanol

HRID 1886719노트

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HRID 1886719 반응식
[CH2:1]([O:5][C:6]1[C:7]([F:13])=[C:8]([F:12])[CH:9]=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH3:4].C([Li])(CC)C.[O:19]1[C:23]2([CH2:28][CH2:27][CH:26]([CH:29]3[CH2:34][CH2:33][C:32](=[O:35])[CH2:31][CH2:30]3)[CH2:25][CH2:24]2)[O:22][CH2:21][CH2:20]1.[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C>[O:19]1[C:23]2([CH2:24][CH2:25][CH:26]([CH:29]3[CH2:34][CH2:33][C:32]([C:9]4[CH:10]=[CH:11][C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[C:7]([F:13])[C:8]=4[F:12])([OH:35])[CH2:31][CH2:30]3)[CH2:27][CH2:28]2)[O:22][CH2:21][CH2:20]1

참가 물질

7

반응물 4

HCID 25517Ammonium ChlorideHCID 8109134-(1,4-Dioxa-spiro(4.5)dec-8-yl)-cyclohexanoneHCID 27829391-Butoxy-2,3-DifluorobenzeneHCID 178418400CID 53628100

생성물 1

HCID 666825234-(1,4-Dioxaspiro[4.5]decan-8-yl)-1-(4-butoxy-2,3-difluorophenyl)-cyclohexanol수율 99.6%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

3-Butoxy-1,2-difluorobenzene (7) (10.0 g) and THF (200 ml) were added to a reaction vessel under an atmosphere of nitrogen, and cooled to −74° C. sec-Butyllithium (1.00 M, in n-hexane and cyclohexane solution; 64.0 ml) was added dropwise in the temperature range of −74° C. to −70° C., and the stirring was continued for another 2 hours. Successively, 4-(1,4-dioxaspiro[4.5]decan-8-yl)-cyclohexanone (21) (12.8 g) in THF (50 ml) solution was added dropwise in the temperature range of −75° C. to −70° C., while the mixture was allowed to come to 25° C. The reaction mixture was poured into a 3%-aqueous solution of ammonium chloride (100 ml) and ethyl acetate (100 ml) in a vessel and mixed with them. The mixture was then allowed to stand until it had separated into two phases of organic and aqueous phases, and the extraction into an organic phase was carried out. The resulting organic phase was separated, and washed successively with water, a saturated aqueous solution of sodium hydrogencarbonate and water, and then dried over anhydrous magnesium sulfate. The solvent was then distilled off under reduced pressure to leave 4-(1,4-dioxaspiro[4.5]decan-8-yl)-1-(4-butoxy-2,3-difluorophenyl)-cyclohexanol (22) (22.7 g). The resulting compound (22) was a pale yellow oil.

후처리

  1. additionwas added dropwise in the temperature range of −74° C. to −70° C.
  2. customto come to 25° C
  3. additionmixed with them
  4. customhad separated into two phases of organic and aqueous phases
  5. extractionthe extraction into an organic phase
  6. customThe resulting organic phase was separated
  7. washwashed successively with water
  8. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and water, and then dried over anhydrous magnesium sulfate
  9. distillationThe solvent was then distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-3234bb206660487796acc281d3390ee0
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501038B2

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