Hydrochloric Acid → HCID 57425852, compound

HRID 1641502Notes

Reaction equation

HRID 1641502 reaction equation
[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

Participants

9

Reactant 6

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

Product 1

HCID 57425852HCID 57425852, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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))

Sources & evidence

ORD record
ord-afb362228b754e8389bac906c6f3cf5c
Source dataset
uspto-grants-2012_02
Patent number
US08114994B2

Reaction notes

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