Hydrochloric Acid → HCID 68510790, compound

HRID 1990897Notes

Reaction equation

HRID 1990897 reaction equation
C([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[C:8]([O:19][CH2:20][CH3:21])[CH:7]=1)=O)C.[H-].C([Al+]CC(C)C)C(C)C.Cl>C1COCC1>[CH2:20]([O:19][C:8]1[CH:7]=[C:6]([CH2:4][OH:3])[CH:11]=[CH:10][C:9]=1[C:12]1[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=1)[CH3:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 68507568HCID 68507568, compound

Product 1

HCID 68510790HCID 68510790, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-ethoxy-4′-fluoro-biphenyl-4-carboxylic acid ethyl ester (0.50 g, 1.73 mmol, 1.0 equiv) in anhydrous THF (10 mL) was added slowly over a time period of 15 min under cooling to −10° C. a solution of diisobutylaluminium hydride (5.2 mL, 5.20 mmol, 3.0 equiv; 1 M solution in hexane). After 1 h, the reaction mixture was poured on ice, the pH adjusted to 4 by addition of a 1 M solution of HCl, the solution extracted with ethyl acetate (2×100 mL) and the combined organic phases washed with water (2×100 mL) and a conc. solution of sodium chloride (100 mL). The organic phase was dried over MgSO4, concentrated by evaporation under reduced pressure to give 0.42 g (99%) of the title compound which was directly used in the consecutive step without further purification.

Workup

  1. additionthe reaction mixture was poured on ice
  2. extractionthe solution extracted with ethyl acetate (2×100 mL)
  3. washthe combined organic phases washed with water (2×100 mL)
  4. dry with materialThe organic phase was dried over MgSO4
  5. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-1593958e59104f3ea22b52a48a54ee3f
Source dataset
uspto-grants-2010_01
Patent number
US07645753B2

Reaction notes

Loading…