Sodium Carbonate → HCID 71093194, compound

HRID 332672Notes

Reaction equation

HRID 332672 reaction equation
Br[C:2]1[CH:13]=[CH:12][C:5]([CH2:6][CH:7]2[O:11][CH2:10][CH2:9][O:8]2)=[CH:4][CH:3]=1.B(O)(O)[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]=[O:22])[CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+].[BH4-].[Na+]>O1CCOCC1.O.CO>[O:8]1[CH2:9][CH2:10][O:11][CH:7]1[CH2:6][C:5]1[CH:12]=[CH:13][C:2]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][OH:22])[CH:16]=2)=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 27343563-Formylphenylboronic acidHCID 27569562-[(4-bromophenyl)methyl]-1,3-dioxolaneHCID 4311764Sodium borohydride

Product 1

HCID 71093194HCID 71093194, compoundYield 52.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
125 °C

Procedure

A mixture of 2-(4-bromobenzyl)-1,3-dioxolane (2.0 g, 8.2 mmol), 3-formylboronic acid (2.45 g, 16.4 mmol), tetrakis-(triphenylphosphine)palladium (0) (0.763 g, 0.66 mmol), and sodium carbonate (1.74 g, 16.4 mmol) in dioxan/water (15 mL/3 mL) in a microwave vessel was degassed in a stream of nitrogen for 10 minutes. The vessel was sealed and heated in the microwave at 125° C. for 30 minutes. The solvent was decanted off, and the solid residues washed with ethyl acetate. The organic phases were combined, and the solvent evaporated at reduced pressure. The crude material was purified by silica gel chromatography eluting with 100% iso-hexane to 50% ethyl acetate in iso-hexane to afford an oil. The oil was dissolved in methanol (25 mL) and cooled to 0° C. Sodium borohydride (0.393 g, 10.4 mmol) was added portion-wise, and the reaction mixture was stirred at 0° C. for 30 minutes followed by 1 hour at ambient temperature. The reaction mixture was quenched with water and extracted twice with ethyl acetate. The combined organic extracts were dried with anhydrous magnesium sulfate, and the solvent evaporated at reduced pressure. The crude material was purified by silica gel chromatography eluting with 100% iso-hexane to 100% ethyl acetate in iso-hexane to afford the title compound (1.16 g, 52%).

Workup

  1. customwas degassed in a stream of nitrogen for 10 minutes
  2. customThe vessel was sealed
  3. customThe solvent was decanted off
  4. washthe solid residues washed with ethyl acetate
  5. customthe solvent evaporated at reduced pressure
  6. customThe crude material was purified by silica gel chromatography
  7. washeluting with 100% iso-hexane to 50% ethyl acetate in iso-hexane
  8. customto afford an oil
  9. temperaturecooled to 0° C
  10. waitfollowed by 1 hour at ambient temperature
  11. customThe reaction mixture was quenched with water
  12. extractionextracted twice with ethyl acetate
  13. dry with materialThe combined organic extracts were dried with anhydrous magnesium sulfate
  14. customthe solvent evaporated at reduced pressure
  15. customThe crude material was purified by silica gel chromatography
  16. washeluting with 100% iso-hexane to 100% ethyl acetate in iso-hexane

Sources & evidence

ORD record
ord-0efbcbd4f500439bbcd0c6acd9dee531
Source dataset
uspto-grants-2014_11
Patent number
US08877774B2

Reaction notes

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