Hydrochloric Acid → HCID 10615819, compound

HRID 1884320Notes

Reaction equation

HRID 1884320 reaction equation
[CH2:1]([C:4]1[C:13]([CH3:14])=[C:12]2[C:7]([C:8]([CH3:17])([CH3:16])[CH2:9][C:10](=[O:15])[O:11]2)=[C:6]([CH3:18])[C:5]=1[O:19][CH2:20][O:21][CH3:22])[CH:2]=[CH2:3].B.C1C[O:27]CC1.[OH-].[Na+].OO.Cl>C1COCC1.O>[OH:27][CH2:3][CH2:2][CH2:1][C:4]1[C:13]([CH3:14])=[C:12]2[C:7]([C:8]([CH3:16])([CH3:17])[CH2:9][C:10](=[O:15])[O:11]2)=[C:6]([CH3:18])[C:5]=1[O:19][CH2:20][O:21][CH3:22]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 2723981Borane;tetrahydrofuranHCID 10494728HCID 10494728, compound

Product 1

HCID 10615819HCID 10615819, compoundYield 195.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Compound D (4.09 g, 13.46 mmol) was dissolved in 7 mL of freshly distilled THF. Argon was passed through the mixture for 20 min. The solution was cooled in an ice-water bath. BH3—THF solution (1.0 M, 5.05 mL, 5.05 mmol) was added dropwise with stirring. After the addition, the mixture was stirred at 0° C. for 2 h. Water (about 1 mL) was added dropwise to destroy the excess borane until hydrogen evolution ceased. NaOH solution (2 N, 3.4 mL) and 30% H2O2 solution (1.7 mL, 16.2 mmol) were added. The mixture was stirred for 30 min and neutralized with 5% HCl solution. The organic compounds were extracted with EtOAc (3×50 mL), washed with water (3×30 mL), and dried over MgSO4. The solvent was evaporated, and the residue was purified on a silica gel column (EtOAc/hexanes=1/3, v/v) to give 3.19 g (70%) of the product. 1H NMR (CDCl3) δ4.91 (s, 2H), 3.63 (s, 3H), 3.60 (t, J=6.0 Hz, 2H), 2.81 (t, J=7.4 Hz, 2H), 2.56 (s, 2H), 2.38 (s, 3H), 2.24 (s, 3H), 1.77 (m, 2H), 1.45 (s, 6H).

Workup

  1. temperatureThe solution was cooled in an ice-water bath
  2. additionAfter the addition
  3. stirringthe mixture was stirred at 0° C. for 2 h
  4. customto destroy the excess borane until hydrogen evolution
  5. extractionThe organic compounds were extracted with EtOAc (3×50 mL)
  6. washwashed with water (3×30 mL)
  7. dry with materialdried over MgSO4
  8. customThe solvent was evaporated
  9. customthe residue was purified on a silica gel column (EtOAc/hexanes=1/3

Sources & evidence

ORD record
ord-4f35fdf082174a489307cbe8c6529b6d
Source dataset
uspto-grants-2004_07
Patent number
US06764768B2

Reaction notes

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