Triethylamine → HCID 67301399, compound

HRID 643585Notes

Reaction equation

HRID 643585 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10](=[O:14])[C:11]([OH:13])=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].C(N(CC)CC)C>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C@@H:10]([OH:14])[C:11]([OH:13])=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 150240293-(3,4-dichlorophenyl)-2-oxopropanoic acid

Product 1

HCID 67301399HCID 67301399, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-35 °C

Procedure

A solution of 12.2 g (38.0 mmol) (1R)—B-chlorodiisopinocampheylborane in 20 mL THF was added dropwise within 30 min to a solution of 8.0 g (34.3 mmol) 3-(3,4-dichloro-phenyl)-2-oxo-propionic acid and 5.2 mL (38.0 mmol) triethylamine in 40 mL THF cooled to −35° C. and the reaction mixture was kept for 1 h at this temperature. The cooling bath was removed and the reaction solution was stirred for 4 h at RT. Then the reaction solution was carefully combined with 50 mL 1 M NaOH (exothermic) and 30 mL TBME at 5-10° C. and stirred for 15 min. The organic phase was separated off and extracted with 25 mL water and 15 mL 1 M NaOH. The combined aqueous phases were acidified with 2 M HCl and extracted three times with in each case 40 mL TBME. The combined organic phases were dried over Na2SO4 and evaporated down i. vac. The residue was dissolved in 80 mL boiling water and suction filtered through Celite. The filtrate was saturated with NaCl and extracted three times with EtOAc. The combined organic phases were filtered through Na2SO4 and again evaporated down i. vac. The crude product was further reacted without purification.

Workup

  1. customThe cooling bath was removed
  2. customwas carefully combined with 50 mL 1 M NaOH (exothermic) and 30 mL TBME at 5-10° C.
  3. stirringstirred for 15 min
  4. customThe organic phase was separated off
  5. extractionextracted with 25 mL water and 15 mL 1 M NaOH
  6. extractionextracted three times with in each case 40 mL TBME
  7. dry with materialThe combined organic phases were dried over Na2SO4
  8. customevaporated down i
  9. dissolutionThe residue was dissolved in 80 mL
  10. filtrationfiltered through Celite
  11. extractionextracted three times with EtOAc
  12. filtrationThe combined organic phases were filtered through Na2SO4
  13. customagain evaporated down i
  14. customThe crude product was further reacted without purification

Sources & evidence

ORD record
ord-d94d8b002d294f639a4eb8d7244b3f75
Source dataset
uspto-grants-2010_04
Patent number
US07700598B2

Reaction notes

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