Triethylamine → HCID 118659535, compound

HRID 1477241Notes

Reaction equation

HRID 1477241 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([OH:14])=[O:13])[CH:6]=[CH:5]2.[C:15]([C@@H:17]1[CH2:19][C@H:18]1[CH2:20][OH:21])#[CH:16].C(N(CC)CC)C>O1CCCC1.[Cu]I.[Cl-].[Cl-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd+2]>[OH:21][CH2:20][C@@H:18]1[CH2:19][C@H:17]1[C:15]#[C:16][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([OH:14])=[O:13])[CH:6]=[CH:5]2

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 45498526-Bromo-2-naphthalenecarboxylic acidHCID 129387989HCID 129387989, compound

Product 1

HCID 118659535HCID 118659535, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 84124Bis(triphenylphosphine)palladium chlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 6-bromo-2-naphthoic acid (6.1, 1.0 g, 4.0 mmol), racemic ((trans)-2-ethynylcyclopropyl)methanol (1.7, 0.5 g, 5.2 mmol), copper(I) iodide (30 mg, 0.16 mmol) and palladium(II) bis(triphenylphosphine)dichloride (56 mg, 0.08 mmol) in tetrahydrofuran (7.5 mL) under a nitrogen atmosphere was added triethylamine (2.5 mL) and the reaction was stirred for 1 week. The reaction was partitioned between 2N aqueous sodium hydroxide and ethyl acetate. The aqueous layer was acidified with conc HCl and extracted with ethyl acetate. The organic layer was washed with water, saturated sodium chloride and dried over magnesium sulfate, filtered and concentrated under reduced pressure to give 6-(((trans)-2-(hydroxymethyl)cyclopropyl)ethynyl)-2-naphthoic acid (6.2, 1.0 g, 94%).

Workup

  1. customThe reaction was partitioned between 2N aqueous sodium hydroxide and ethyl acetate
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water, saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5a134f3fdee840a3b078efb528014d0d
Source dataset
uspto-grants-2016_08
Patent number
US09403758B2

Reaction notes

Loading…