Triethylamine → HCID 68608764, compound

HRID 642837Notes

Reaction equation

HRID 642837 reaction equation
[CH3:1][C:2]1[C:7]2[O:8][CH2:9][CH2:10][O:11][C:6]=2[CH:5]=[C:4]([CH2:12][C:13](=[O:17])[C:14]([OH:16])=[O:15])[CH:3]=1.C(N(CC)CC)C>C1COCC1>[OH:17][C@H:13]([CH2:12][C:4]1[CH:3]=[C:2]([CH3:1])[C:7]2[O:8][CH2:9][CH2:10][O:11][C:6]=2[CH:5]=1)[C:14]([OH:16])=[O:15]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 45122021HCID 45122021, compound

Product 1

HCID 68608764HCID 68608764, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-35 °C

Procedure

Under a nitrogen atmosphere a solution of 15.1 g (47.0 mmol) (1R)—B-chlorodiisopinocampheylborane in 50 mL THF was added dropwise within 15 min to a solution of 9.2 g (38.9 mmol) 3-(8-methyl-2,3-dihydro-1,4-benzodioxin-6-yl)-2-oxo-propionic acid and 5.4 mL (39.0 mmol) triethylamine in 100 mL THF cooled to −35° C. and the reaction mixture was stirred for 1 h at RT. After the end of the reaction the reaction solution was evaporated down i.vac., combined with 200 mL 1 M NaOH and 150 mL TBME, stirred, the aqueous phase was separated off, acidified with 2 M HCl and extracted twice with 250 mL EtOAc. The combined organic phases were dried, filtered through activated charcoal and evaporated down i.vac.

Workup

  1. customAfter the end of the reaction the reaction solution
  2. customwas evaporated down i.vac
  3. stirringstirred
  4. customthe aqueous phase was separated off
  5. extractionextracted twice with 250 mL EtOAc
  6. customThe combined organic phases were dried
  7. filtrationfiltered through activated charcoal
  8. customevaporated down i.vac

Sources & evidence

ORD record
ord-03cd1225c86840bcaf03c6341c206ebc
Source dataset
uspto-grants-2010_04
Patent number
US07696195B2

Reaction notes

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