Hydrochloric Acid → HCID 57425852、化合物

HRID 1727314ノート

反応式

HRID 1727314 の反応式
[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

参加物

9

反応物 6

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

生成物 1

HCID 57425852HCID 57425852、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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=2/1, 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.

後処理

  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=2/1, 1.44 g, 85%, Rf=0.16 (Hexane:EtOAc=3:1))

出典と根拠

ORDレコード
ord-4df3589b49834623afbf76ac541b366e
出典データセット
uspto-grants-2009_02
特許番号
US07495006B2

反応ノート

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