Hydrochloric Acid → HCID 178419208, 화합물

HRID 2244948노트

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HRID 2244948 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 an 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 min. Sodium borohydride (0.72 g, 3.1 equivalents) was added, and the mixture was stirred at room temperature for 1 hr. Then bis(3,5-di-tert-butyl-4-methoxyphenyl)phosphine oxide (3.0 g, 6.16 mmoL) synthesized in Reference Example 7 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 hrs. Water (10 mL) was added at 3° C., and toluene (30 mL) and 6M—HCl (20 mL) were added. The mixture was stirred at room temperature for 30 min. The reaction mixture was partitioned and the aqueous layer was extracted with toluene (30 mL). The combined organic layer was washed successively with 5% aqueous NaCl solution (20 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered by gravity, and 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 give the title compound (1.18 g, white crystals). yield 39.6%. melting point: 134.7° C. 1H-NMR (300 MHz, CDCl3, TMS) δ: 0.37-1.08 (m. 3H), 1.39 (s, 36H), 3.69 (s, 6H), 6.23 (dq, 1H, J=376.2 Hz, 6.78 Hz), 7.50 (d, 4H, J=12.18 Hz).

후처리

  1. additionwere successively added at 5° C.
  2. stirringthe mixture was stirred at room temperature for 18 hrs
  3. stirringThe mixture was stirred at room temperature for 30 min
  4. customThe reaction mixture was partitioned
  5. extractionthe aqueous layer was extracted with toluene (30 mL)
  6. washThe combined organic layer was washed successively with 5% aqueous NaCl solution (20 mL)
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. filtrationfiltered by gravity
  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-fd00bf8d45b34bea9c182b63545caeae
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07678942B2

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