Hydrochloric Acid → HCID 57425852, 화합물

HRID 1641502노트

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HRID 1641502 반응식
[CH2:1]=[C:2]1[CH2:5][CH:4]([CH2:6][O:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:3]1.B1C2CCCC1CCC2.[OH-:24].[Na+].OO.Cl.[NH4+].[Cl-]>O.C1COCC1>[OH:24][CH2:1][CH:2]1[CH2:5][CH:4]([CH2:6][O:7][CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:3]1

참가 물질

9

반응물 6

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 57425851HCID 57425851, 화합물

생성물 1

HCID 57425852HCID 57425852, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

In a 10 mL flask with 1-methylene-3-benzyloxymethyl-cyclobutane (1.54 g, 8.19 mmol) inside, dry THF 11 mL was added under argon to give a colorless solution. Then cool this to 0° C., 9-BBN (0.5 M in THF, 27.4 mL, 13.7 mmol) was added drop by drop. This was allowed to warm up to ambient temperature and was left stirring for 22 hr, after which time the reaction mixture was cooled to 0° C. and H2O (0.9 mL), 3 N NaOH (2.7 mL) and 30% H2O2 (2.8 mL) were added successively. After stirring for 1 hr, 2 N HCl and saturated NH4Cl were added. The mixture was extracted with EtOAc and the separated organic phase was dried over MgSO4 and solvent evaporation gave the crude oily product, which was purified by silica gel flash chromatography (Hexane: EtOAc=3:1) to give a colorless oil (cis/trans=211, 1.44 g, 85%, Rf=0.16 (Hexane: EtOAc=3:1)). 1H NMR (CDCl3, 400 MHz): δ 1.52-1.60 (m), 1.86-1.90 (m), 2.12-2.19 (m), 2.36-2.64 (m), 3.39-3.41 (d, J=8), 3.49-3.51 (d, J=8), 3.54-3.56 (d, J=8), 3.64-3.66 (d, J=8), 4.51 (s), 4.53 (s), 7.2-7.4 (m). MS (FAB): expected for C13H18O2 (M+H)+ 207.28. Found 207.13807.

후처리

  1. customto give a colorless solution
  2. temperatureto warm up to ambient temperature
  3. waitwas left
  4. temperatureafter which time the reaction mixture was cooled to 0° C.
  5. stirringAfter stirring for 1 hr
  6. extractionThe mixture was extracted with EtOAc
  7. dry with materialthe separated organic phase was dried over MgSO4 and solvent evaporation
  8. customgave the crude oily product, which
  9. customwas purified by silica gel flash chromatography (Hexane: EtOAc=3:1)
  10. customto give a colorless oil (cis/trans=211, 1.44 g, 85%, Rf=0.16 (Hexane: EtOAc=3:1))

출처 및 근거

ORD 기록
ord-afb362228b754e8389bac906c6f3cf5c
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08114994B2

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