Hydrochloric Acid → HCID 178419208, 화합물

HRID 720769노트

반응식

HRID 720769 반응식
[Cl-].[Ce+3].[Cl-].[Cl-].[BH4-:5].[Na+].[C:7]([C:11]1[CH:12]=[C:13]([PH:23](=O)[C:24]2[CH:29]=[C:28]([C:30]([CH3:33])([CH3:32])[CH3:31])[C:27]([O:34][CH3:35])=[C:26]([C:36]([CH3:39])([CH3:38])[CH3:37])[CH:25]=2)[CH:14]=[C:15]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:16]=1[O:17][CH3:18])([CH3:10])([CH3:9])[CH3:8].[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>C1COCC1.C1(C)C=CC=CC=1.O>[C:30]([C:28]1[CH:29]=[C:24]([PH:23][C:13]2[CH:12]=[C:11]([C:7]([CH3:10])([CH3:9])[CH3:8])[C:16]([O:17][CH3:18])=[C:15]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:14]=2)[CH:25]=[C:26]([C:36]([CH3:39])([CH3:38])[CH3:37])[C:27]=1[O:34][CH3:35])([CH3:31])([CH3:32])[CH3:33].[BH3:5]

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 24636Cerium(III) chlorideHCID 4311764Sodium borohydrideHCID 21226445Aluminium lithium hydrideHCID 178490127HCID 178490127, 화합물

생성물 1

HCID 178419208HCID 178419208, 화합물수율 39.6%

시약·촉매·용매 3

HCID 962Water용매HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매

실험 절차

Under argon atmosphere, a solution of cerium chloride (4.55 g, 3.0 equivalents) in THF (25 mL) was stirred at room temperature (25° C.) for 30 minutes. After sodium borohydride (0.72 g, 3.1 equivalents) was added, the mixture was stirred at room temperature for 1 hour. Then, bis(3,5-di-tert-butyl-4-methoxyphenyl)phosphine oxide (3.0 g, 6.16 mmol) synthesized in Reference Example 3 and lithium aluminum hydride (0.28 g, 1.2 equivalents) were successively added at 5° C., and the mixture was stirred at room temperature for 18 hours. After water (10 mL) was added at 3° C. and toluene (30 mL) and 6M-HCl (20 mL) were then added, the mixture was stirred at room temperature for 30 minutes. The reaction solution was allowed to separate into layers. An aqueous layer was extracted with toluene (30 mL). Organic layers were combined, washed with a 5% NaCl aqueous solution (20 mL), dried over anhydrous magnesium sulfate and then naturally filtered. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (alumina 25 g, n-hexane). The residue was recrystallized from heptane to obtain the title compound (1.18 g, white crystal). Yield 39.6%, mp. 134.7° C.

후처리

  1. additionwere successively added at 5° C.
  2. stirringthe mixture was stirred at room temperature for 18 hours
  3. stirringthe mixture was stirred at room temperature for 30 minutes
  4. customto separate into layers
  5. extractionAn aqueous layer was extracted with toluene (30 mL)
  6. washwashed with a 5% NaCl aqueous solution (20 mL)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationnaturally filtered
  9. concentrationThe filtrate was concentrated under reduced pressure
  10. customThe residue was purified by column chromatography (alumina 25 g, n-hexane)
  11. customThe residue was recrystallized from heptane

출처 및 근거

ORD 기록
ord-ff84fc9c43e9432783a18a5bbb04d877
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07135582B2

반응 노트

불러오는 중…