Triethylamine → HCID 67301514, compound

HRID 643591Notes

Reaction equation

HRID 643591 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH2:9][C:10](=[O:14])[C:11]([OH:13])=[O:12])=[CH:4][C:3]=1[CH3:15].C(N(CC)CC)C.[OH-].[Na+].CC(OC)(C)C>C1COCC1>[Cl:1][C:2]1[C:3]([CH3:15])=[CH:4][C:5]([CH2:9][C@@H:10]([OH:14])[C:11]([OH:13])=[O:12])=[CH:6][C:7]=1[CH3:8]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 15413tert-Butyl methyl etherHCID 67301556HCID 67301556, compound

Product 1

HCID 67301514HCID 67301514, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

12.3 g (54.4 mmol) 3-(4-chloro-3,5-dimethyl-phenyl)-2-oxo-propionic acid in 130 mL THF and 7.6 mL (54.4 mmol) triethylamine were combined at −35° C. with a solution of 21.0 g (65.3 mmol) (1R)—B-chlorodiisopinocampheylborane in 65 mL THF within 30 min and stirred for 2 h at this temperature. After the reaction had ended the reaction mixture was made alkaline at 0° C. with 50 mL 1 M NaOH (exothermic), stirred for 3 h, combined with 30 mL TBME and the phases were separated. The organic phase was washed with 50 mL water and 30 mL 1 M NaOH. The combined aqueous phases were acidified with 2 M HCl and extracted with TBME. The organic phases were dried over Na2SO4 and evaporated down i. vac. The product was reacted further without purification.

Workup

  1. customat 0° C.
  2. stirringstirred for 3 h
  3. customthe phases were separated
  4. washThe organic phase was washed with 50 mL water and 30 mL 1 M NaOH
  5. extractionextracted with TBME
  6. dry with materialThe organic phases were dried over Na2SO4
  7. customevaporated down i
  8. customThe product was reacted further without purification

Sources & evidence

ORD record
ord-f3a502036c464c118a0afcc3593524c4
Source dataset
uspto-grants-2010_04
Patent number
US07700598B2

Reaction notes

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